Dichloromethane → HCID 86590816, compound

HRID 1592958Notes

Reaction equation

HRID 1592958 reaction equation
F[C:2](F)(F)C(O)=O.[F:8][C:9]([F:49])([F:48])[C:10]1[CH:11]=[C:12]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[CH2:13][N:14]([CH3:40])[C:15]([N:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[CH2:28][CH2:27][N:26](C(=O)C)[CH2:25][CH2:24]2)[CH2:19][C@@H:18]1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[CH3:39])=[O:16].C(Cl)[Cl:51]>>[ClH:51].[F:49][C:9]([F:8])([F:48])[C:10]1[CH:11]=[C:12]([C@H:13]([N:14]([CH3:40])[C:15]([N:17]2[CH2:22][CH2:21][C@H:20]([N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)[CH2:19][C@@H:18]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])=[O:16])[CH3:2])[CH:41]=[C:42]([C:44]([F:47])([F:45])[F:46])[CH:43]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 51002993HCID 51002993, compound

Product 1

HCID 86590816HCID 86590816, compound

Procedure

Trifluoroacetic acid (1 mL) was added drop-wise at 0° C. to a solution of compound 2 (48 mg) in dry DCM (3 mL). The solution was stirred for 1 hour at the same temperature and for 1 hour at r.t. Then the solvent was removed in vacuo and the crude dissolved in AcOEt (5 mL). The resulting solution was washed with a saturated potassium carbonate solution and dried. After concentration in vacuo, the crude 2-(R)-(4-fluoro-2-methyl-phenyl)-4-(S)-piperazin-1-yl-piperidine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methylamide (18 mg) was dissolved in dry Et2O (1 mL) and was then treated with hydrochloric acid (1M in Et2O—220 μL) at 0° C. The resulting mixture was stirred at r.t. for 30 minutes, then filtered and triturated with n-pentane to give the title compound as a whitish solid (15 mg).

Workup

  1. customThen the solvent was removed in vacuo
  2. dissolutionthe crude dissolved in AcOEt (5 mL)
  3. washThe resulting solution was washed with a saturated potassium carbonate solution
  4. customdried
  5. concentrationAfter concentration in vacuo
  6. dissolutionthe crude 2-(R)-(4-fluoro-2-methyl-phenyl)-4-(S)-piperazin-1-yl-piperidine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methylamide (18 mg) was dissolved in dry Et2O (1 mL)
  7. additionwas then treated with hydrochloric acid (1M in Et2O—220 μL) at 0° C
  8. stirringThe resulting mixture was stirred at r.t. for 30 minutes
  9. filtrationfiltered
  10. customtriturated with n-pentane

Sources & evidence

ORD record
ord-e48b51eea6f444a899d9cfa0824e583c
Source dataset
uspto-grants-2007_11
Patent number
US07294630B2

Reaction notes

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