Cyclopropylamine → HCID 25144382, compound

HRID 500171Notes

Reaction equation

HRID 500171 reaction equation
C([N:4](CC)[CH:5]([CH3:7])[CH3:6])(C)C.OC(C(F)(F)F)=O.[N:17]1[C:26]2[C:21](=[CH:22][C:23]([C:27]3([C:30]4[N:34]5[CH:35]=[C:36]([C:39]6[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=6)[C:42]([OH:44])=O)[CH:37]=[N:38][C:33]5=[N:32][CH:31]=4)[CH2:29][CH2:28]3)=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C1(N)CC1.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:5]1([NH:4][C:42](=[O:44])[C:41]2[CH:45]=[CH:46][CH:47]=[C:39]([C:36]3[CH:37]=[N:38][C:33]4[N:34]([C:30]([C:27]5([C:23]6[CH:22]=[C:21]7[C:26](=[CH:25][CH:24]=6)[N:17]=[CH:18][CH:19]=[CH:20]7)[CH2:29][CH2:28]5)=[CH:31][N:32]=4)[CH:35]=3)[CH:40]=2)[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 131728268HCID 131728268, compound

Product 1

HCID 25144382HCID 25144382, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (194 μL, 1.11 mmol) was added to a mixture of 3-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid TFA salt (126.9 mg, 0.2 mmol), cyclopropylamine (17.1 mg, 0.3 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (97.3 mg, 0.22 mmol) in N,N-dimethylformamide (1.0 mL). The mixture was stirred at RT for 3 h, and was diluted with methanol (0.8 mL). The resulting solution was purified by RP-HPLC (pH=10) to give the desired product. LCMS: (M+H)=446.1.

Workup

  1. customThe resulting solution was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-77dd974e64e14cd99211a61199d0651e
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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