Sodium Hydroxide → HCID 86700220, compound

HRID 879414Notes

Reaction equation

HRID 879414 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH3:28])[N:23]=[C:22]4[C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH3:28])[N:23]=[C:22]4[C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86700218HCID 86700218, compound

Product 1

HCID 86700220HCID 86700220, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a vial was dissolved (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(pyridin-3-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate (69 mg, 0.11 mmol) in THF (2 mL) and EtOH (1 mL). 1M NaOH (1 mL) was added, and the mixture was heated to 50° C. for 15 hours. The reaction was cooled to 23° C., 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 light yellow powder. LCMS-ESI+: calc'd for C33H30ClN4O3S: 597.1 (M+H+); Found: 597.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 9.32 (s, 1H), 8.89 (d, J=8.1 Hz, 1H), 8.72 (d, J=4.5 Hz, 1H), 8.66 (s, 1H), 8.09 (dd, J=8.9, 1.4 Hz, 1H), 7.95 (dd, J=7.9, 5.5 Hz, 1H), 7.79 (s, 1H), 7.76-7.67 (m, 2H), 7.63-7.52 (m, 3H), 5.26 (s, 1H), 4.17 (s, 3H), 2.61 (s, 3H), 0.98 (s, 9H).

Workup

  1. temperatureThe reaction was cooled to 23° C.
  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-c577c289d21b48a48228634eb5dd0d5b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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