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Cyclopropanecarbonyl chloride → HCID 68488744, compound

HRID 1891211
Notes
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Reaction equation

HRID 1891211 reaction equation
[F:1][C:2]1[C:3]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[CH:32][CH:31]=2)=[C:4]([C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH:51]1([C:54](Cl)=[O:55])[CH2:53][CH2:52]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:51]1([C:54]([N:39]2[CH2:40][CH2:41][CH:36]([C:33]3[CH:32]=[CH:31][C:30]([CH2:29][O:28][C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[C:8]4[N:13]=[C:12]([N:14]5[C:18]([C:19]([F:21])([F:22])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]5)[CH:11]=[CH:10][CH:9]=4)=[CH:35][CH:34]=3)[CH2:37][CH2:38]2)=[O:55])[CH2:53][CH2:52]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 68486762HCID 68486762, compound

Product 1

HCID 68488744HCID 68488744, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 516892
Sodium Bicarbonate
Solvent

Procedure

To a solution of the title compound from Example 5 Step C (40 mg, 0.07 mmol) in DCM (1 mL) were added diisopropyl ethyl amine (0.12 mL, 0.70 mmol) and cyclopropanecarbonyl chloride (0.02 mL, 0.21 mmol). The reaction mixture was stirred for 1 h at ambient temperature, then was diluted with sat. aq. NaHCO3 and extracted with DCM. The organic phase was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The product was used in the subsequent step without further purification: LCMS m/z 636.8 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-a7f542aaea5a4bc1813cee5b4c9bb4c2
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507512B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes