Sodium Hydroxide → HCID 86700181, compound

HRID 879373Notes

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:24]=[CH:23][N:22]=[C:21]([C:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]([CH3:34])[N:26]=4)[CH:20]=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.CO>[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:24]=[CH:23][N:22]=[C:21]([C:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]([CH3:34])[N:26]=4)[CH:20]=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

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-indazol-3-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (13.5 mg, 0.022 mmol) in THF (0.5 mL) and methanol (0.5 mL) was added 1N NaOH solution (0.5 mL, excess). The reaction mixture was stirred at 50° C. for 2 h and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C33H30ClN4O3S: 597.2; found: 597.2. 1H NMR (400 MHz, CDCl3) δ 9.21 (d, J=5.6 Hz, 1H), 8.93 (s, 1H), 8.59 (d, J=7.6 Hz, 1H), 8.22 (d, J=5.2 Hz, 1H), 8.07 (s, 1H), 7.75 (d, J=6.8 Hz, 1H), 7.60-7.46 (m, 6H), 5.36 (s, 1H), 4.29 (s, 3H), 2.65 (s, 3H), 1.02 (s, 9H).

Workup

custompurified by reverse phase HPLC
washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record: ord-091783c4f2cf4f2dab048cfa090e40df
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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