Cyclopropanecarbonyl chloride → HCID 67001731, compound

HRID 1186243Notes

Reaction equation

HRID 1186243 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-73826e13f7c241b29677472609f2d36b
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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