Phenyl chloroformate → (4-{[Methyl-(3-methyl-pyrazine-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid phenyl ester

HRID 1685028Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]([CH3:18])[C:9]([C:11]2[C:16]([CH3:17])=[N:15][CH:14]=[CH:13][N:12]=2)=[O:10])[N:6]=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.C1COCC1>[C:23]1([O:22][C:20](=[O:21])[NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][N:8]([CH3:18])[C:9]([C:11]3[C:16]([CH3:17])=[N:15][CH:14]=[CH:13][N:12]=3)=[O:10])[N:6]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of N-((2-aminothiazol-4-yl)methyl)-N,3-dimethylpyrazine-2-carboxamide (555 mg, 1.84 mmol) and DMAP (20 mg) in pyridine (10 mL) was cooled to 0° C. and a solution of phenyl chloroformate (433 mg, 2.8 mmol) in THF was added drop wise. The mixture was stirred overnight and all volatiles were removed in vacuo at 30° C. The residue was triturated with TBME to afford (4-{[Methyl-(3-methyl-pyrazine-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid phenyl ester (125 mg) as a tan colored solid (purity 96%).

Workup

customall volatiles were removed in vacuo at 30° C
customThe residue was triturated with TBME

Sources & evidence

ORD record: ord-1c18361e42ab450686be6dd049c8ff95
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148380B2

Reaction notes

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