Ethanol → HCID 86700224, compound

HRID 879419Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:11]1[C:36]([CH3:37])=[CH:35][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]4C3C(C)=NC=CC=3)[S:17][C:13]=2[C:12]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:47][CH2:48]O>C1COCC1>[C:1]([O:5][C@@H:6]([C:11]1[C:36]([CH3:37])=[CH:35][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:48]3[CH:47]=[CH:16][N:15]=[CH:14][CH:13]=3)[S:17][C:13]=2[C:12]=1[C:38]1[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

In a vial was dissolved (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(2-methylpyridin-3-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate (100 mg, 0.16 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 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. LCMS-ESI+: calc'd for C33H30ClN4O3S: 597.2 (M+H+); Found: 597.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.77 (d, J=6.1 Hz, 2H), 8.73 (s, 1H), 8.47 (d, J=6.3 Hz, 2H), 8.06 (d, J=8.9 Hz, 1H), 7.78-7.70 (m, 3H), 7.60 (dt, J=11.1, 7.5 Hz, 3H), 5.26 (s, 1H), 4.18 (s, 3H), 2.61 (s, 3H), 0.98 (s, 9H).

Workup

temperatureThe reaction was cooled to 23° C.
filtrationfiltered
filtration(0.45 micron teflon syringe filter)
customThe filtrate was purified by reverse phase HPLC
washeluting with 5-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record: ord-a8c771e507c348a7b69d8fd2df4ca180
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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