4-Fluorobenzoyl chloride → HCID 178501180, compound

HRID 518601Notes

Reaction equation

HRID 518601 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[N:16]([C@@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18]2)[C:15]2[CH:27]=[C:28]([CH2:31][O:32][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:30][C:14]=2[N:13]=1>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[N:16]([C@@H:17]3[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18]3)[C:15]3[CH:27]=[C:28]([CH2:31][O:32][Si:33]([CH:34]([CH3:36])[CH3:35])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])[CH:29]=[CH:30][C:14]=3[N:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 178501188HCID 178501188, compound

Product 1

HCID 178501180HCID 178501180, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-fluorobenzoyl chloride (0.113 mL, 0.957 mmol) in DCM (2.90 mL) was cooled to 0° C. under nitrogen. To this was added cis-methyl 4-(2-amino-6-((triisopropylsilyloxy)methyl)-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (0.4 g, 0.870 mmol) followed by TEA (0.482 mL, 3.48 mmol). The resulting mixture was stirred at 0° C. for 30 minutes. The ice bath was removed, and the mixture was stirred for 2 hours. The reaction mixture was diluted with DCM (20 mL) and washed with water (10 mL). The organic layer was collected, dried over sodium sulfate, concentrated, and dried under vacuum to afford cis-methyl 4-(2-(4-fluorobenzamido)-6-((triisopropylsilyloxy)methyl)-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (0.5 g, 100% yield).

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred for 2 hours
  3. additionThe reaction mixture was diluted with DCM (20 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2a62da506db146ffbf89e0bbad848197
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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