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

HRID 1257831Notes

Reaction equation

HRID 1257831 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-d267a1c8d8b343458ee1f07ac25c2acc
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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