Trifluoroacetic acid → HCID 178484136, compound

HRID 2040654Notes

Reaction equation

HRID 2040654 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:60]=[CH:59][C:15]2[NH:16][C:17]([CH2:19][CH2:20][CH:21]3[CH2:24][CH:23]([N:25]([CH2:27][C@@H:28]4[C@H:32]5[O:33]C(C)(C)[O:35][C@H:31]5[C@H:30]([N:38]5[C:42]6[N:43]=[CH:44][N:45]=[C:46]([NH:47]CC7C=CC(OC)=CC=7OC)[C:41]=6[CH:40]=[CH:39]5)[CH2:29]4)[CH3:26])[CH2:22]3)=[N:18][C:14]=2[CH:13]=1)([CH3:11])([CH3:10])[CH3:9].C([SiH](CC)CC)C>O>[NH2:47][C:46]1[C:41]2[CH:40]=[CH:39][N:38]([C@@H:30]3[CH2:29][C@H:28]([CH2:27][N:25]([CH:23]4[CH2:22][CH:21]([CH2:20][CH2:19][C:17]5[NH:16][C:15]6[CH:59]=[CH:60][C:12]([C:8]([CH3:9])([CH3:10])[CH3:11])=[CH:13][C:14]=6[N:18]=5)[CH2:24]4)[CH3:26])[C@@H:32]([OH:33])[C@H:31]3[OH:35])[C:42]=2[N:43]=[CH:44][N:45]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178491011HCID 178491011, compound

Product 1

HCID 178484136HCID 178484136, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic Acid (5 ml) added to a mixture of Water (0.5 ml) and 7-((3aS,4R,6R,6aR)-6-(((3-(2-(5-(tert-butyl)-1H-benzo[d]imidazol-2-yl)ethyl)cyclobutyl)(methyl)amino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.20 g, 0.28 mmol) at RT. The reaction was allowed to proceed overnight upon which it was quenched with Triethylsilane (0.088 ml, 0.55 mmol). The volatiles were removed in vacuo and resulting residue was partitioned between saturated NaHCO3 and DCM/MeOH (10:1). Aqueous extracted 3× more with DCM/MeOH (10:1) and combined organics were dried over MgSO4, filtered, concentrated and purified by flash chromatography (DCM/7N NH3 in MeOH 87:13) to give the desired product as an off-white foam (0.060 g). MS (ESI−) for C30H41N7O2 m/z 532.3 [M+H]+; MS (ESI−) for C30H41N7O2 m/z 530.4 [M−H]−; HPLC purity >94% (ret. time, 2.723 min.)

Workup

  1. customThe volatiles were removed in vacuo
  2. customresulting residue
  3. customwas partitioned between saturated NaHCO3 and DCM/MeOH (10:1)
  4. extractionAqueous extracted 3× more with DCM/MeOH (10:1)
  5. dry with materialcombined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography (DCM/7N NH3 in MeOH 87:13)

Sources & evidence

ORD record
ord-18124b4607f24b46acf46cc62e325774
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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