Cyclobutylamine → N-cyclobutyl-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzamide
Reaction equation
C(N(CC)C(C)C)(C)C.Cl.Cl.[N:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3([C:25]4[N:29]5[CH:30]=[C:31]([C:34]6[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=6)[CH:32]=[N:33][C:28]5=[N:27][CH:26]=4)[CH2:24][CH2:23]3)=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[CH:43]1([NH2:47])[CH2:46][CH2:45][CH2:44]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.CO>[CH:43]1([NH:47][C:38](=[O:39])[C:37]2[CH:36]=[CH:35][C:34]([C:31]3[CH:32]=[N:33][C:28]4[N:29]([C:25]([C:22]5([C:18]6[CH:17]=[C:16]7[C:21](=[CH:20][CH:19]=6)[N:12]=[CH:13][CH:14]=[CH:15]7)[CH2:24][CH2:23]5)=[CH:26][N:27]=4)[CH:30]=3)=[CH:42][CH:41]=2)[CH2:46][CH2:45][CH2:44]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
N,N-Diisopropylethylamine (30.0 μL, 0.172 mmol) was added to a mixture of 4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid dihydrochloride (18.5 mg, 0.0386 mmol), cyclobutanamine (4.12 mg, 0.0579 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (20.5 mg, 0.0463 mmol) in N,N-dimethylformamide (1 mL). The mixture was stirred at RT for 3 h, and diluted with methanol (0.8 mL). The resulting solution was purified by RP-HPLC (pH 10) to give the desired product. LCMS: (M+H)=460.1.
Workup
- customThe resulting solution was purified by RP-HPLC (pH 10)
Sources & evidence
- ORD record
- ord-34024c7665fe478a8e29eead8577af44
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767675B2
Reaction notes
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