Methyl chloroformate → HCID 71280654, compound

HRID 1497944Notes

Reaction equation

HRID 1497944 reaction equation
Cl.[NH2:2][C:3]1([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:32])=[C:18]([NH:20][C:21]([C:23]4[N:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]5=[N:25][CH:24]=4)=[O:22])[CH:19]=3)[N:10]=2)[CH2:6][C:5]([F:8])([F:7])[CH2:4]1.Cl[C:34]([O:36][CH3:37])=[O:35]>N1C=CC=CC=1>[F:7][C:5]1([F:8])[CH2:6][C:3]([NH:2][C:34](=[O:35])[O:36][CH3:37])([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:32])=[C:18]([NH:20][C:21]([C:23]4[N:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]5=[N:25][CH:24]=4)=[O:22])[CH:19]=3)[N:10]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 71280501HCID 71280501, compound

Product 1

HCID 71280654HCID 71280654, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of N-(5-(5-(1-amino-3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide hydrochloride (166) in anhydrous pyridine (1 mL) at 0° C. was added drop-wise methyl chloroformate (19 uL, 0.26 mmol). The reaction was stirred to room temperature for 20 minutes. The crude was concentrated and purified by preparative HPLC to yield methyl (3,3-difluoro-1-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)cyclobutyl)carbamate (F174). MS m/z 483.1 (M+1)+.

Workup

  1. concentrationThe crude was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b4652fb7c8c74a5db28b114a478bfe9f
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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