4-Fluorobenzoyl chloride → HCID 178491275, compound

HRID 518677Notes

Reaction equation

HRID 518677 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[CH2:12][CH2:11][C@H:10]([C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH:21]=[CH:22][C:4]=2[N:3]=1.[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>C(Cl)Cl>[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([N:1]([C:38](=[O:39])[C:37]2[CH:41]=[CH:42][C:34]([F:33])=[CH:35][CH:36]=2)[C:2]2[N:6]([C@H:7]3[CH2:12][CH2:11][C@@H:10]([C:13](=[O:14])[NH:15][CH:16]([CH3:18])[CH3:17])[CH2:9][CH2:8]3)[C:5]3[CH:19]=[C:20]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[CH:21]=[CH:22][C:4]=3[N:3]=2)=[O:39])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 178491277HCID 178491277, compound

Product 1

HCID 178491275HCID 178491275, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-4-(2-amino-6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-1-yl)-N-isopropylcyclohexanecarboxamide (424 mg, 0.971 mmol) and 4-fluorobenzoyl chloride (0.172 mL, 1.457 mmol) in DCM was added TEA (0.271 mL, 1.943 mmol), and the resulting mixture was stirred at RT for 10 minutes. The mixture was evaporated, and the residue diluted with DCM, washed with water, brine, and the organic layer dried over Na2SO4. The mixture was purified via flash chromatography using a linear gradient of 0% to 10% MeOH in DCM. The title compound was obtained as a tan foam (442 mg, max 80% yield, mixture of the mono and bis-acylated products).

Workup

  1. customThe mixture was evaporated
  2. additionthe residue diluted with DCM
  3. washwashed with water, brine
  4. dry with materialthe organic layer dried over Na2SO4
  5. customThe mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-336734cd6f154b39adc5aba86e6c5511
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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