Trichloroacetyl chloride → HCID 69314912, compound

HRID 2053748Notes

Reaction equation

HRID 2053748 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH3:29])=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.C(N(CC)C(C)C)(C)C.[Cl:39][C:40]([Cl:45])([Cl:44])[C:41](Cl)=[O:42]>ClCCl>[Cl:39][C:40]([Cl:45])([Cl:44])[C:41]([C:3]1[N:4]2[C:5]([CH2:6][N:7]([C:15](=[O:16])[C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH3:29])=[CH:21][CH:22]=3)[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10]2)=[CH:1][CH:2]=1)=[O:42]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 10199923HCID 10199923, compound

Product 1

HCID 69314912HCID 69314912, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(2-methyl-cyclohex-1-en-1-yl)-phenyl]-methanone of Step D (1 g, 2.21 mmol) and N,N-diisopropylethylamine (0.770 mL, 4.42 mmol) were combined in anhydrous dichloromethane (11.1 mL) and trichloroacetyl chloride (0.740 mL, 6.63 mmol) was added dropwise. After stirring at room temperature for four hours, the solvent was removed and the residue dissolved in ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated and the residue purified by flash column chromatography. Recrystallization from petroleum ether afforded 1.21 g of the title compound as white crystals, m.p. 171° C.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified by flash column chromatography
  8. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-83fd4271be414ebb83e9f9889e984717
Source dataset
uspto-grants-2008_02
Patent number
US07326700B2

Reaction notes

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