Cyclopropanecarbonyl chloride → HCID 67001731, compound

HRID 2279238Notes

Reaction equation

HRID 2279238 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[N:7]1[C:17]2[N:16]3[CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH:15]3[CH2:14][CH2:13][NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH:1]1([C:4]([N:12]2[CH2:13][CH2:14][CH:15]3[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][CH2:18][N:16]3[C:17]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]2=3)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 67001762HCID 67001762, compound

Product 1

HCID 67001731HCID 67001731, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cyclopropylcarbonyl chloride (0.072 mL, 0.79 mmol) CH2Cl2 (1 mL) was added to an ice-cooled solution of the product of Example 72A (218 mg, 0.716 mmol) in CH2Cl2 (5 mL). The reaction was stirred with ice cooling under nitrogen for 45 minutes and then it was allowed to warm to room temperature for 4 hours. The reaction was quenched by addition of methanol (2 mL) and the solution was stirred for 10 minutes. The reaction mixture was then concentrated under vacuum. The residue was purified by HPLC (30×100 mm, C18, Waters XBridge™ column eluted with 0.1 M aqueous (NH4)2CO3-methanol, 80:20-0:100 over 15 minutes) to provide the title compound: MS (DCI) m/z 373 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of methanol (2 mL)
  2. stirringthe solution was stirred for 10 minutes
  3. concentrationThe reaction mixture was then concentrated under vacuum
  4. customThe residue was purified by HPLC (30×100 mm, C18, Waters XBridge™ column eluted with 0.1 M aqueous (NH4)2CO3-methanol, 80:20-0:100 over 15 minutes)

Sources & evidence

ORD record
ord-bfae21e3aaa9424cbfd16e6aaca91381
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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