Acetyl chloride → HCID 66938544, compound

HRID 1716912Notes

Reaction equation

HRID 1716912 reaction equation
C([Cl:4])(=O)C.C(OC([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:35])[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[Cl:34])[CH:20]=2)[CH2:14][CH2:13]1)=O)(C)(C)C>CO>[ClH:4].[ClH:34].[Cl:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[C:26]([NH:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([NH:18][CH:15]2[CH2:14][CH2:13][NH:12][CH2:17][CH2:16]2)[CH:20]=1)=[O:35]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58997258HCID 58997258, compound

Product 1

HCID 66938544HCID 66938544, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine acetyl chloride (5 ml) and dried methanol (10 ml) at 0° C. under a nitrogen atmosphere. Stir for 1 hr. at 0° C. Add a solution of 4-(3-(2-Chloro-4-fluorobenzoylamino) phenylamino)piperidine-1-carboxylic acid t-butyl ester (Preparation 56, 72 mg, 0.161 mmol) in methanol (2 mL). Stir overnight. Concentrate under reduced pressure. Triturate with diethyl ether (1 mL) to provide a pale yellow foam of the title compound: mp 255-7° C.; mass spectrum (ion spray): m/z=348.2 (M+1). Analysis calc'd for C18H21Cl3FN3O.1.0H2O: C, 49.28; H, 5.28; N, 9.58. Found: C, 49.15; H, 4.96; N, 9.56.

Workup

  1. customat 0° C.
  2. customat 0° C
  3. stirringStir overnight
  4. concentrationConcentrate under reduced pressure
  5. customTriturate with diethyl ether (1 mL)

Sources & evidence

ORD record
ord-d4ff6ee26ef446898f4caa4ae7de2751
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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