Phenyl chloroformate → Phenyl carbamate

HRID 1042052Notes

Reaction equation

HRID 1042052 reaction equation
[NH2:1]C1N=C(C2CCN(C(=O)CN3C(C)=CC(C(F)(F)F)=N3)CC2)SC=1.C(N(C(C)C)CC)(C)C.[C:35]1([O:41][C:42](Cl)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[C:35]1([O:41][C:42](=[O:43])[NH2:1])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 669564011-[4-(4-Amino-thiazol-2-yl)-piperidin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone

Product 1

HCID 69322Phenyl carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(4-amino-thiazol-2-yl)-piperidin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone (80 mg, 0.21 mmol) in dichloromethane (5 mL) is added diisopropylethylamine (0.053 mL, 0.25 mmol), and subsequently phenylchloroformate (0.033 mL, 0.21 mmol) at 0° C. After stirring overnight at RT, solvents are evaporated under reduced pressure and the residue is purified by column chromatography on silica gel (ethyl acetate/heptane 7:3) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-carbamic acid phenyl ester (Compound No. I.g.023, 71 mg, 67%). 1H-NMR (400 MHz, CDCl3): δ=1.57-1.78 (m, 2H), 2.08-2.19 (m, 2H), 2.22 (s, 3H), 2.75-2.81 (m, 1H), 3.05-3.20 (m, 2H), 3.95-3.99 (m, 1H), 4.44-4.52 (m, 1H), 4.83-4.98 (2d, 2H, diastereotopic protons), 6.25 (s, 1H), 7.05-7.20 (m, 3H), 7.29-7.38 (m, 2H), 7.95 (br, 1H). MS: m/z=494 (M+1).

Workup

  1. customsolvents are evaporated under reduced pressure
  2. customthe residue is purified by column chromatography on silica gel (ethyl acetate/heptane 7:3)

Sources & evidence

ORD record
ord-ce0a2c36b5c841f7a5c432447ffaec11
Source dataset
uspto-grants-2013_10
Patent number
US08557821B2

Reaction notes

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