Lithium Hydroxide → 3-(3-{3-t-Butyl-5-[(isoquinoline-3-carbonyl)-amino]-pyrazol-1-yl)-phenyl)-propionic acid

HRID 1270524Notes

Reaction equation

HRID 1270524 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:19]([C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:20])=[CH:16][C:15]([C:31]([CH3:34])([CH3:33])[CH3:32])=[N:14]2)[CH:8]=1)C.[Li+].[OH-]>CO>[C:31]([C:15]1[CH:16]=[C:17]([NH:18][C:19]([C:21]2[N:22]=[CH:23][C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])[N:13]([C:9]2[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:35])=[O:3])[CH:12]=[CH:11][CH:10]=2)[N:14]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 451215353-(3-{3-t-Butyl-5-[(isoquinoline-3-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester

Product 1

HCID 184498933-(3-{3-t-Butyl-5-[(isoquinoline-3-carbonyl)-amino]-pyrazol-1-yl)-phenyl)-propionic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 156 (47 mg, 0.1 mmol) and 2N LiOH (3 mL) in MeOH (3 mL) was stirred at RT overnight. The reaction mixture was neutralized to pH=4, and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine, and dried (NaSO4) and filtered. The filtrate was concentrated to afford 3-(3-{3-t-butyl-5-[(isoquinoline-3-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid, (39 mg, 88%). 1H NMR (CDCL3): 10.49 (s, 1H), 9.16 (s, 1H), 8.69 (s, 1H), 8.03 (d, J=7.6 Hz, 2H), 7.81 (t, J=7.2 Hz, 1H), 7.73 (t, J=7.2 Hz, 1H), 7.48–7.39 (m, 3H), 7.28 (br s, 1H), 6.94 (s, 1H), 3.02 (t, J=7.6 Hz, 2H), 2.79 (t, J=7.6 Hz, 2H), 1.42 (s, 9H); MS (ESI) m/z: 442 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1abd04b9118241b6b0ee82ac6464bf88
Source dataset
uspto-grants-2007_04
Patent number
US07202257B2

Reaction notes

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