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Dimethylformamide → 8-(6-(3,5-bis(trifluoromethyl)phenyl)benzo[d][1,3]dioxol-5-ylthio)-9-(3-(isopropylamino)propyl)-9H-purin-6-amine

HRID 521582
Notes
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Reaction equation

HRID 521582 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:18][CH:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]1[C:34]([S:35][C:36]2[CH:41]=[C:40]3[O:42][CH2:43][O:44][C:39]3=[CH:38][C:37]=2I)=[N:33][C:27]2[C:28]([NH2:32])=[N:29][CH:30]=[N:31][C:26]1=2)[CH3:20].C([O-])(O)=O.[Na+].CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:37]2[C:36]([S:35][C:34]3[N:25]([CH2:24][CH2:23][CH2:22][NH:21][CH:19]([CH3:20])[CH3:18])[C:26]4[C:27]([N:33]=3)=[C:28]([NH2:32])[N:29]=[CH:30][N:31]=4)=[CH:41][C:40]3[O:42][CH2:43][O:44][C:39]=3[CH:38]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 516892Sodium BicarbonateHCID 9549213Zelavespib

Product 1

HCID 872747508-(6-(3,5-bis(trifluoromethyl)phenyl)benzo[d][1,3]dioxol-5-ylthio)-9-(3-(isopropylamino)propyl)-9H-purin-6-amine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst
HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

3,5-Bis(trifluoromethyl)phenylboronic acid (22.6 mg, 0.0877 mmol) was added to PU-H71 (30 mg, 0.0585 mmol) and NaHCO3 (14.7 mg, 0.1755 mmol). DMF (0.5 mL) was added and the reaction mixture was evacuated and back filled with nitrogen. This was repeated four times then nitrogen was bubbled through the reaction mixture for 10 minutes. Then H2O (0.1 mL) and Pd(PPh3)2Cl2 (4 mg, 0.00584 mmol) were added and the reaction mixture was heated under nitrogen at 90° C. for 3 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAc:MeOH—NH3 (7N), 4:5:2:1) to give 24.4 mg (70%) of DZ2-391. 1H NMR (500 MHz, CDCl3) δ 8.22 (s, 1H), 7.79 (s, 3H), 7.12 (s, 1H), 6.86 (s, 1H), 6.09 (s, 2H), 5.71 (br s, 2H), 4.07 (t, J=6.6 Hz, 2H), 2.82 (septet, J=6.2 Hz, 1H), 2.49 (t, J=6.5 Hz, 2H), 1.95 (m, 2H), 1.12 (d, J=6.3 Hz, 6H); 13C NMR (125 MHz, CDCl3) δ 154.1, 152.3, 151.5, 149.6, 148.6, 147.5, 142.1, 137.2, 131.2 (q, J=33 Hz), 129.6, 123.1 (q, J=270 Hz), 121.3, 119.6, 119.4, 114.9, 110.8, 102.4, 49.5, 42.8, 40.6, 28.8, 21.7; HRMS (ESI) m/z [M+H]+ calcd. for C26H25F6N6O2S, 599.1664; found. 599.1653; HPLC: method A Rt=7.45, method B Rt=9.38.

Workup

  1. customthe reaction mixture was evacuated
  2. additionback filled with nitrogen
  3. customnitrogen was bubbled through the reaction mixture for 10 minutes
  4. customSolvent was removed under reduced pressure
  5. customthe resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAc:MeOH—NH3 (7N), 4:5:2:1)
  6. customto give 24.4 mg (70%) of DZ2-391

Sources & evidence

ORD record
ord-ac670ead7127415281e63d6f39473c76
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328114B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes