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3-[3-({[(3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(methyl)amino)cyclobutyl]-N-[2-amino-4-(1-methoxy-2-methylpropan-2-yl)phenyl]propanamide → HCID 178494914, compound

HRID 511683
Notes
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Reaction equation

HRID 511683 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][N:22]([CH3:45])[CH:23]2[CH2:26][CH:25]([CH2:27][CH2:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([CH3:43])([CH3:42])[CH2:39][O:40][CH3:41])=[CH:34][C:33]=3[NH2:44])=O)[CH2:24]2)[O:12]1>CC(O)=O>[CH3:41][O:40][CH2:39][C:38]([C:35]1[CH:36]=[CH:37][C:32]2[NH:31][C:29]([CH2:28][CH2:27][CH:25]3[CH2:24][CH:23]([N:22]([CH2:21][C@@H:13]4[C@H:14]5[O:18][C:17]([CH3:19])([CH3:20])[O:16][C@H:15]5[C@H:11]([N:6]5[CH:5]=[N:4][C:3]6[C:7]5=[N:8][CH:9]=[N:10][C:2]=6[NH2:1])[O:12]4)[CH3:45])[CH2:26]3)=[N:44][C:33]=2[CH:34]=1)([CH3:42])[CH3:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 677750013-[3-({[(3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(methyl)amino)cyclobutyl]-N-[2-amino-4-(1-methoxy-2-methylpropan-2-yl)phenyl]propanamide

Product 1

HCID 178494914HCID 178494914, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

3-[3-({[(3aR,4R,6R,6aR)-6-(6-Amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl}(methyl)amino)cyclobutyl]-N-[2-amino-4-(1-methoxy-2-methylpropan-2-yl)phenyl]propanamide (1.036 g, 1.66 mmol) was dissolved in AcOH (17 ml) and heated to 50° C. for 5 h. The reaction was concentrated in vacuo and the residue was dissolved in DCM (75 ml) and sat. NaHCO3 solution (75 ml) was added. The organic layer was separated and the aqueous layer was extracted with DCM (2×75 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product as a dark orange oil (0.850 g, 94%). The product was purified using neutral prep-HPLC to give the product as a pale yellow oil (0.485 g, 47%, 88% pure): MS (ESI+) for C32H44N8O4 m/z 605.4 [M+H]+; LC purity 88% (ret. time, 1.25 min); 1H NMR (500 MHz, CDCl3) δH 10.44 (dd, J=207.7, 22.9 Hz, 1H), 8.41 (d, J=17.1 Hz, 1H), 8.16 (d, J=13.8 Hz, 1H), 7.89-7.58 (m, 1H), 7.54-7.29 (m, 2H), 6.15 (d, J=10.9 Hz, 1H), 5.92-5.56 (m, 3H), 4.98 (d, J=12.5 Hz, 1H), 4.76-4.39 (m, 1H), 3.47 (d, J=6.2 Hz, 2H), 3.33 (d, J=4.8 Hz, 3H), 2.98-2.43 (m, 4H), 2.42-2.00 (m, 6H), 1.99-1.88 (m, 2H), 1.77-1.66 (m, 1H), 1.64 (s, 3H), 1.61-1.48 (m, 1H), 1.44 (d, J=8.1 Hz, 3H), 1.40 (d, J=7.9 Hz, 6H), 1.28 (dd, J=16.0, 9.0 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM (75 ml)
  3. additionsat. NaHCO3 solution (75 ml) was added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with DCM (2×75 ml)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product as a dark orange oil (0.850 g, 94%)
  10. customThe product was purified

Sources & evidence

ORD record
ord-6cc66f72a26b4a5f868cc80d1f24d187
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096634B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes