Sodium Hydroxide → (S)-2-(2-(2-(1H-indazol-1-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

HRID 879371Notes

Reaction equation

[N:1]1([C:10]2[CH:15]=[C:14]([C:16]3[S:17][C:18]4[C:24]([C:25]5[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=5)=[C:23]([C@H:32]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:33]([O:35]CC)=[O:34])[C:22]([CH3:43])=[CH:21][C:19]=4[N:20]=3)[CH:13]=[CH:12][N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+]>C1COCC1.CO>[N:1]1([C:10]2[CH:15]=[C:14]([C:16]3[S:17][C:18]4[C:24]([C:25]5[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=5)=[C:23]([C@H:32]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[C:33]([OH:35])=[O:34])[C:22]([CH3:43])=[CH:21][C:19]=4[N:20]=3)[CH:13]=[CH:12][N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (S)-ethyl 2-(2-(2-(1H-indazol-1-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (6.8 mg, 0.011 mmol) in THF (0.4 mL) and methanol (0.4 mL) was added 1N NaOH solution (0.4 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 C32H28ClN4O3S: 583.2; found: 583.3. 1H NMR (400 MHz, CDCl3) δ 8.86 (d, J=8.8 Hz, 1H), 8.63 (d, J=4.8 Hz, 1H), 8.57 (s, 1H), 8.23 (s, 1H), 7.97 (s, 1H), 7.81-7.77 (m, 2H), 7.73 (d, J=7.6 Hz, 1H), 7.58-7.50 (m, 4H), 7.30 (t, J=7.2 Hz, 1H), 5.35 (s, 1H), 2.61 (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-017dd49209804278987405d89870670a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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