Cyclohexylamine → HCID 25143836, compound

HRID 500160Notes

Reaction equation

HRID 500160 reaction equation
C(N(CC)CC)C.[N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3([C:21]4[N:25]5[CH:26]=[C:27]([C:30]([OH:32])=O)[CH:28]=[N:29][C:24]5=[N:23][CH:22]=4)[CH2:20][CH2:19]3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.F[P-](F)(F)(F)(F)F.[N:40]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.C1(N)CCCCC1>CN(C)C=O.CO>[CH:44]1([NH:40][C:30]([C:27]2[CH:28]=[N:29][C:24]3[N:25]([C:21]([C:18]4([C:14]5[CH:13]=[C:12]6[C:17](=[CH:16][CH:15]=5)[N:8]=[CH:9][CH:10]=[CH:11]6)[CH2:20][CH2:19]4)=[CH:22][N:23]=3)[CH:26]=2)=[O:32])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:43]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 67224940HCID 67224940, compound

Product 1

HCID 25143836HCID 25143836, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (13.9 μL, 0.1 mmol) was added to a mixture of 3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidine-6-carboxylic acid (8.26 mg, 0.025 mmol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (14.3 mg, 0.0275 mmol) and cyclohexanamine (5.7 μL, 0.05 mmol) in N,N-dimethylformamide (0.5 mL) at RT. The mixture was stirred at RT for 2 h, and diluted with methanol (1.3 mL). The resulting solution was purified by RP-HPLC to give the desired product. LCMS: (M+H)=412.1.

Workup

  1. customThe resulting solution was purified by RP-HPLC

Sources & evidence

ORD record
ord-ea8d9d1d86b548ac97f5fd9e3a301b91
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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