HCID 52933910, compound → HCID 52934135, compound

HRID 1024477Notes

Reaction equation

HRID 1024477 reaction equation
[C:1]([C:3]([C:6]1[CH:36]=[CH:35][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:23][C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30]C)=[O:29])=[O:25])=[N:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2]>C1COCC1.CO.O.[OH-].[Li+]>[C:1]([C:3]([C:6]1[CH:36]=[CH:35][C:9]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[S:23][C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:33])[CH3:34])[C:28]([OH:30])=[O:29])=[O:25])=[N:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:8][CH:7]=1)([CH3:4])[CH3:5])#[N:2]

Participants

5

Reactant 1

HCID 52933910HCID 52933910, compound

Product 1

HCID 52934135HCID 52934135, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 168937Lithium hydroxide, monohydrateSolvent

Procedure

To methyl 2-(5-(4-(4-(2-cyanopropan-2-yl)benzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 85, 65 mg) in THF (1 ml), methanol (1 ml) and 1M lithium hydroxide monohydrate (0.51 ml) was added and reaction mixture was stirred overnight at RT. Organic solvent was concentrated and added water, dilute HCl was added under stirring to pH acidic. The reaction mixture was filtered, to obtain the title compound. Yield: 22 mg (35%). 1HNMR (DMSO-d6, 300 MHz): δ 13.0 (bs, 1H), 10.49 (s, 1H), 8.4 (s, 1H), 8.37 (d, 1H), 8.04 (d, 2H), 7.93 (d, 2H), 7.81 (d, 2H), 7.71 (d, 2H), 4.31 (m, 1H), 2.25 (m, 1H), 1.74 (s, 6H), 0.97 (m, 6H); MS (ES+) m/z 491.2 (M+1).

Workup

  1. customreaction mixture
  2. concentrationOrganic solvent was concentrated
  3. additionadded water, dilute HCl
  4. additionwas added
  5. stirringunder stirring
  6. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-7f4be3bdcc0e4a52bfdffa93ced91cef
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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