Cyclopentanecarbonyl chloride → HCID 57849869, compound

HRID 737163Notes

Reaction equation

HRID 737163 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)=[CH:21][N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][C:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:36]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:37])=[CH:27][CH:28]=2)=[CH:21][N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 57849851HCID 57849851, compound2×

Product 1

HCID 57849869HCID 57849869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (S)-2-[5-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5111, Example 111, 0.05 g, 0.12 mmol), Cyclopentanecarbonyl chloride (0.015 mL), and TEA (0.018 mL) in dichloromethane (3 mL) was stirred at 0° C. for 20 min. then was quenched with water. The mixture was concentrated in vacuo and the resulting residue was dissolved in DMF (5 mL) and water (0.5 mL) then purified by reverse phase prep. LC/MS to furnish the desired product; MS: 519.1 (M+H+).

Workup

  1. customthen was quenched with water
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in DMF (5 mL)
  4. customwater (0.5 mL) then purified by reverse phase prep

Sources & evidence

ORD record
ord-d8f66f84a7c24652bf204678598e3883
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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