Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(pyridin-2-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879424Notes

Reaction equation

HRID 879424 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:35]([CH3:36])=[CH:34][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH3:27])[N:22]=[C:21]4[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[S:17][C:13]=2[C:12]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CCO>[C:1]([O:5][C@@H:6]([C:11]1[C:35]([CH3:36])=[CH:34][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH3:27])[N:22]=[C:21]4[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[S:17][C:13]=2[C:12]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86700227(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(pyridin-2-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700229(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(pyridin-2-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a vial was dissolved (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(pyridin-2-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate (122 mg, 0.2 mmol) in THF (3 mL) and EtOH (1.5 mL). 1M NaOH (1.5 mL) was added, and the mixture was heated to 50° C. overnight. The reaction was cooled to rt, and filtered (0.45 micron teflon syringe filter). The filtrate was purified by reverse phase HPLC, eluting with 5-100% acetonitrile in H2O with 0.1% TFA to give the desired product as a bright yellow powder. LCMS-ESI+: calc'd for C33H30ClN4O3S: 597.1 (M+H+); Found: 597.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.79 (s, 1H), 8.66 (d, J=4.7 Hz, 1H), 8.33 (d, J=8.1 Hz, 1H), 8.23 (dd, J=11.1, 4.5 Hz, 1H), 8.02 (dd, J=8.9, 1.3 Hz, 1H), 7.76 (s, 1H), 7.75-7.68 (m, 1H), 7.65-7.53 (m, 5H), 5.26 (s, 1H), 4.14 (s, 3H), 2.61 (s, 3H), 0.98 (s, 9H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered
  3. filtration(0.45 micron teflon syringe filter)
  4. customThe filtrate was purified by reverse phase HPLC
  5. washeluting with 5-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record
ord-07e97e57312e4f19b9d8750077aa51dd
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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