Lithium Hydroxide → [4-(6-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazin-1-yl]-acetic acid hydrochloride salt

HRID 902656Notes

Reaction equation

HRID 902656 reaction equation
C[O:2][C:3](=[O:48])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[C:38]=3[Cl:47])[CH2:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:12]=2)[CH2:7][CH2:6]1.[Li+].[OH-]>C1COCC1.O>[ClH:47].[Cl:47][C:38]1[C:39]([C:43]([F:44])([F:45])[F:46])=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][N:21]([CH2:22][CH:23]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:20][CH2:19][CH2:18][O:17][C:13]1[N:12]=[C:11]([N:8]2[CH2:7][CH2:6][N:5]([CH2:4][C:3]([OH:48])=[O:2])[CH2:10][CH2:9]2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69253888[4-(6-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazin-1-yl]-acetic Acid Methyl Ester

Product 1

HCID 69254330[4-(6-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazin-1-yl]-acetic acid hydrochloride salt

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of [4-(6{-3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-pyridin-2-yl)-piperazin-1-yl]-acetic acid methyl ester (46 mg, 0.07 mmol) in THF (2 ml) and H2O (0.5 ml) was added LiOH (6 mg, 0.13 mmol). The reaction mixture was stirred for 24 h at RT and then concentrated. The aqueous mixture was acidified to pH=3 with 1 N HCl (aq) and extracted with EtOAc (three times). The organic extracts were dried over Na2SO4, filtered, and concentrated. The free base was dissolved in dichloromethane and 1 N HCl (Et2O) was added. The solution was concentrated under vacuum to provide the title compound as a white solid, 26 mg (45%). MS (ESI) 667.2 (M+).

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc (three times)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe free base was dissolved in dichloromethane
  7. addition1 N HCl (Et2O) was added
  8. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-aaf10aaeba5f448b9320afd539d347d1
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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