Methyl chloroformate → Methyl 4-{5-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-yl}piperazine-1-carboxylate

HRID 500175Notes

Reaction equation

HRID 500175 reaction equation
CN1CCOCC1.OC(C(F)(F)F)=O.[N:15]1([C:21]2[N:26]=[CH:25][C:24]([C:27]3[CH:28]=[N:29][C:30]4[N:31]([C:33]([C:36]5([C:39]6[CH:40]=[C:41]7[C:46](=[CH:47][CH:48]=6)[N:45]=[CH:44][CH:43]=[CH:42]7)[CH2:38][CH2:37]5)=[CH:34][N:35]=4)[CH:32]=3)=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.Cl[C:50]([O:52][CH3:53])=[O:51]>C(#N)C.CO>[N:45]1[C:46]2[C:41](=[CH:40][C:39]([C:36]3([C:33]4[N:31]5[CH:32]=[C:27]([C:24]6[CH:23]=[CH:22][C:21]([N:15]7[CH2:16][CH2:17][N:18]([C:50]([O:52][CH3:53])=[O:51])[CH2:19][CH2:20]7)=[N:26][CH:25]=6)[CH:28]=[N:29][C:30]5=[N:35][CH:34]=4)[CH2:38][CH2:37]3)=[CH:48][CH:47]=2)[CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 866215066-{1-[6-(6-piperazin-1-ylpyridin-3-yl)imidazo[1,2-a]pyrimidin-3-yl]cyclopropyl}quinoline TFA salt

Product 1

HCID 25144531Methyl 4-{5-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-yl}piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-Methylmorpholine (19.3 μL, 0.175 mmol) was added to a solution of 6-{1-[6-(6-piperazin-1-ylpyridin-3-yl)imidazo[1,2-a]pyrimidin-3-yl]cyclopropyl}quinoline TFA salt (25.0 mg, 0.0292 mmol) in acetonitrile (0.8 mL), followed by addition of methyl chloroformate (3.39 μL, 0.0438 mmol). The mixture was stirred at RT for 30 min, and was diluted with methanol (1.0 mL). The resulting solution was purified by RP-HPLC (pH=10) to give the desired product. LCMS: (M+H)=506.1.

Workup

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

Sources & evidence

ORD record
ord-d24d73c71e9241399d19557f0b5a521c
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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