Lithium Hydroxide → HCID 59618786, compound

HRID 1691448Notes

Reaction equation

HRID 1691448 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[CH:29]=[CH:28][N:27]([CH2:30][C:31]([O:33]C)=[O:32])[N:26]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:35]=[C:36]([C:39]([F:42])([F:41])[F:40])[CH:37]=[CH:38][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C(#N)C.O.[Cl-].[Na+].O.Cl.CCOC(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[CH:29]=[CH:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[N:26]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:35]=[C:36]([C:39]([F:42])([F:40])[F:41])[CH:37]=[CH:38][C:16]=3[CH2:15]2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 2

HCID 3939Lithium HydroxideHCID 66905037HCID 66905037, compound

Product 1

HCID 59618786HCID 59618786, compound

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To methyl-{3-[6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1H-pyrazol-1-yl}acetate (Example 433, 3.5 mg, 0.006 mmol) in acetonitrile (0.5 mL) and water (0.5 mL) was added LiOH (2 mg, 0.005 mmol). After stirring overnight at rt, the reaction was diluted with 2 mL of brine, 0.5 mL of 2N HCl, and 20 mL of EtOAc. The organic layer was separated, washed with water and brine, dried with Na2SO4, and concentrated to give the title compound. 1H NMR (500 MHz, (CD3OD): δ 8.05 (brd s, 1H), 7.91 (brd s, 1H), 7.63 (s, 1H), 7.61 (d, 1H), 7.44 (d, 1H), 7.18 (d, 2H), 7.06 (d, 1H), 7.02 (d, 1H), 6.96 (d, 2H), 5.02 (s, 2H), 1.23 (s, 9H). LCMS: m/e 586.2 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d51e3585224f43f2b262baabb797ec6a
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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