Methanol → N-(1-(4-(2-oxopyrrolidin-1-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

HRID 2175541Notes

Reaction equation

HRID 2175541 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[CH2:11][CH:10]([NH:12][C:13](=[O:30])[CH2:14][NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH2:9]1.O=[C:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:42][CH2:41][CH2:40][C:39]2=[O:43])[CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>C(#N)C>[O:43]=[C:39]1[CH2:40][CH2:41][CH2:42][N:38]1[CH:35]1[CH2:34][CH2:33][CH:32]([N:8]2[CH2:9][CH:10]([NH:12][C:13](=[O:30])[CH2:14][NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:28])([F:27])[F:29])[CH:24]=4)[N:19]=[CH:18][N:17]=3)[CH2:11]2)[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 585626831-(4-Oxocyclohexyl)pyrrolidin-2-oneHCID 86660464N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide TFA salt

Product 1

HCID 68003506N-(1-(4-(2-oxopyrrolidin-1-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide TFA salt (100 mg, 0.22 mmol) from example 1, step G, and 1-(4-oxocyclohexyl)pyrrolidin-2-one (40.5 mg, 0.22 mmol) from above step B, Sodium triacetoxyborohydride (138 mg, 0.64 mmol), were taken in acetonitrile and stirred for 24 h at room temperature. The mixture was treated with MeOH and concentrated under vacuum. The residue was purified by preparative TLC (nBuOH/aq NH4OH 4:1) and reverse phase HPLC to give the title compound as a white solid. ESI-MS (m/z): Calcd. for C24H29F3N6O2: 490.23. found: 491.23 (M+1).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by preparative TLC (nBuOH/aq NH4OH 4:1)

Sources & evidence

ORD record
ord-aea200c7121b4ab79865078b86141b5f
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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