Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

HRID 879386Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[CH:33]=[C:32]([CH3:34])[N:31]([CH3:35])[C:28]5=[N:29][CH:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=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:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[CH:33]=[C:32]([CH3:34])[N:31]([CH3:35])[C:28]5=[N:29][CH:30]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (70 mg, 0.110 mmol) in THF/CH3OH (1.0 mL/1.0 mL) was added 2N NaOH (0.55 mL, 1.1 mmol). The reaction mixture was heated at 50° C. for 2 h and the crude was purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the product. LCMS-ESI+: calc'd for C34H31ClN4O3S: 611.2 (M+H+); Found: 612.2 (M+H+), 1H NMR (400 MHz, CD3OD) δ 8.91 (s, 1H), 8.83 (d, J=5.2 Hz, 1H), 8.65 (s, 1H), 8.60 (s, 1H), 8.08 (d, J=5.6 Hz, 1H), 8.04 (s, 1H), 7.80 (d, J=8.8 Hz, 1H), 7.71 (s, 2H), 5.59 (s, 1H), 5.38 (s, 1H), 3.91 (s, 3H), 2.73 (s, 3H), 2.60 (s, 3H), 1.08 (s, 9H).

Workup

customthe crude was purified by reverse phase HPLC
washeluting by 0-100% acetonitrile in H2O with 0.1% TFA
customto give the product

Sources & evidence

ORD record: ord-c62aec78b8174f78b9c9c88ae6fc2ef2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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