Boron Trichloride → HCID 86597682, compound

HRID 547772Notes

Reaction equation

HRID 547772 reaction equation
C([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH:14][C:15]1[N:20]=[CH:19][C:18]([N:21]([CH3:41])[C:22](=[O:40])[C:23]([C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=2)([CH3:25])[CH3:24])=[C:17]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[Cl:48])[CH:16]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>ClCCl>[F:39][C:36]([F:37])([F:38])[C:28]1[CH:27]=[C:26]([C:23]([CH3:25])([CH3:24])[C:22]([N:21]([C:18]2[CH:19]=[N:20][C:15]([NH:14][C@@H:10]3[CH2:11][CH2:12][CH2:13][C@H:9]3[OH:8])=[CH:16][C:17]=2[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[Cl:48])[CH3:41])=[O:40])[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86597683HCID 86597683, compound

Product 1

HCID 86597682HCID 86597682, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.15 g (0.22 mmol) (1R,2R)—N-[6-(2-benzyloxy-cyclopentylamino)-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide in 2 ml dichloromethane were added 0.87 ml (0.87 mmol) of a 1 M boron trichloride solution in dichloromethane at room temperature. After 2 h the reaction was quenched by addition of 2 ml of a 1 M aqueous hydrochloric acid solution. Neutralisation with 1 M aqueous NaOH solution was followed by extraction with 3 portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 60 mg (46%) of the title compound as an off-white solid.

Workup

  1. customAfter 2 h the reaction was quenched by addition of 2 ml of a 1 M aqueous hydrochloric acid solution
  2. extractionNeutralisation with 1 M aqueous NaOH solution was followed by extraction with 3 portions of tert-butyl methyl ether
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca6ed22b97f447a0be240362002bf2ab
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

Loading…