Phenyl chloroformate → HCID 58267942, compound

HRID 1918111Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10](=[O:13])[NH:11][CH:12]=2)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>>[C:14]([C:4]1[CH:3]=[C:2]([NH:1][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:6]([C:7]2[CH:8]=[CH:9][C:10](=[O:13])[NH:11][CH:12]=2)[N:5]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Reactant 2

HCID 15891Phenyl chloroformate

HCID 222178465-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)pyridin-2(1H)-one

Product 1

HCID 58267942HCID 58267942, compoundYield 12.1%

Procedure

Following the procedure in Example 118A, 5-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)pyridin-2(1H)-one (46 mg, 0.19 mmol) was treated with phenyl chloroformate (0.10 mL, 0.79 mmol) to afford phenyl 3-tert-butyl-1-(6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazol-5-ylcarbamate (8 mg, 0.023 mmol, 12%). 1H NMR (300 MHz, MeOD) δ 7.68 (d, 2H), 7.38 (t, 2H), 7.23 (t, 1H), 7.09 (br s, 2H), 6.63 (d, 1H), 6.34 (s, 1H), 1.30 (s, 9H); LC-MS (ESI) m/z 353 (M+H)+.

Sources & evidence

ORD record: ord-4f0eef342dda4f6a915ea3ec3fb104bd
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618289B2

Reaction notes

Loading…