Lithium Hydroxide → HCID 58864190, compound

HRID 1353425Notes

Reaction equation

HRID 1353425 reaction equation
C([O:4][CH:5]1[C:11]2[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][CH:7]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[C:35]4[C:30](=[CH:31][C:32]([Cl:36])=[CH:33][CH:34]=4)[N:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)(=O)C.[Li+].[OH-]>C1COCC1.O>[Cl:36][C:32]1[CH:31]=[C:30]2[C:35]([C:26]([N:23]3[CH2:24][CH2:25][N:20]([C:18]([NH:17][CH:7]4[CH2:6][CH:5]([OH:4])[C:11]5[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=5[CH2:9][CH2:8]4)=[O:19])[CH2:21][CH2:22]3)=[CH:27][CH:28]=[N:29]2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58864180HCID 58864180, compound

Product 1

HCID 58864190HCID 58864190, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of N-[9-(acetyloxy)-2-fluoro-6,7,8,9-tetrahydro-5H-benzo[α]cyclohepten-7-yl]-4-(7-chloro-4-quinolinyl)-1-piperazinecarboxamide (30.0 mg, 0.0588 mmol) in THF:H2O (3:1, 2 mL) was added LiOH (8 mg). The reaction mixture was stirred at rt for 3 h, then THF was evaporated in vacuo. The reaction mixture was diluted with AcOEt (100 mL), washed with brine, and dried. Concentration followed by flash chromatography afforded the title product. LC-MS: 469 (M++1). δ 1H NMR (CDCl3) δ 8.70 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.45 (d, 1H), 7.05 (m, 2H), 6.85 (m, 2H), 4.95 (m, 1H), 4.35 (m, 1H), 3.65 (m, 4H), 3.20 (m, 4H), 3.15 (m, 1H), 2.60 (m, 1H), 2.20 (m, 2H), 1.8 (m, 3H).

Workup

  1. customTHF was evaporated in vacuo
  2. additionThe reaction mixture was diluted with AcOEt (100 mL)
  3. washwashed with brine
  4. customdried
  5. concentrationConcentration

Sources & evidence

ORD record
ord-194b676aa27a4809b658924c6e8d5253
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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