Hydrochloric Acid → 2-(5-(4-(6-Fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

HRID 1024446Notes

Reaction equation

HRID 1024446 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[S:20][C:19]([C:21]([NH:23][CH:24]([CH:30]([CH3:32])[CH3:31])[C:25]([O:27]CC)=[O:26])=[O:22])=[N:18][CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[S:20][C:19]([C:21]([NH:23][CH:24]([CH:30]([CH3:32])[CH3:31])[C:25]([OH:27])=[O:26])=[O:22])=[N:18][CH:17]=4)=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 52934820Ethyl 2-(5-(4-(6-fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Product 1

HCID 529348192-(5-(4-(6-Fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Ethyl 2-(5-(4-(6-fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 19, 80 mg) in THF (1.6 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (0.32 ml) and the mixture was stirred at RT for 4 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get yellow solid, which was crystallized in ethyl acetate to give the title compound. Yield: 58 mg (77%); 1HNMR (DMSO-d6, 300 MHz): δ 12.99 (bs, 1H), 10.76 (s, 1H), 8.36 (s, 1H), 8.34 (d, 1H), 7.88 (d, 2H), 7.8 (d, 2H), 7.77 (d, 1H), 7.65 (dd, 1H), 7.2 (m, 1H), 4.32, (m, 1H), 2.27 (m, 1H), 0.97 (d, 6H); MS (ES+): m/z 471 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get yellow solid, which
  6. customwas crystallized in ethyl acetate

Sources & evidence

ORD record
ord-053b8fccc1f445bb8793961b35bae020
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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