Methyl chloroformate → HCID 178502010, compound

HRID 215957Notes

Reaction equation

HRID 215957 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH3:31])[C:10]([N:13]2[CH2:30][CH2:29][C:16]3([C:20](=[O:21])[N:19]([C@H:22]4[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)[CH2:15][CH2:14]2)=[N:11][CH:12]=1.C(N(CC)C(C)C)(C)C>C(#N)C.CO>[OH:28][C@@H:25]1[CH2:26][CH2:27][C@H:22]([N:19]2[CH2:18][CH2:17][C:16]3([CH2:29][CH2:30][N:13]([C:10]4[N:11]=[CH:12][C:7]([NH:6][C:2](=[O:3])[O:4][CH3:5])=[CH:8][C:9]=4[CH3:31])[CH2:14][CH2:15]3)[C:20]2=[O:21])[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 178428568HCID 178428568, compound

Product 1

HCID 178502010HCID 178502010, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl chloroformate (6.0 μL) was added to a mixture of 8-(5-amino-3-methylpyridin-2-yl)-2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (18.0 mg) and N,N-diisopropylethylamine (20.0 μL) in acetonitrile (1.0 mL). The mixture was stirred for 2 h, and was diluted with methanol. The resulting solution was purified by prep-HPLC under basic condition to afford methyl {6-[2-(cis-4-hydroxycyclohexyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-methylpyridin-3-yl}carbamate. LCMS: (M+H)+=416.2.

Workup

  1. customThe resulting solution was purified by prep-HPLC under basic condition

Sources & evidence

ORD record
ord-d12e4c07f0164c638e6e212ced788bc2
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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