Sodium Hydroxide → HCID 86699818, compound

HRID 879300Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:11]1[C:29]([CH3:30])=[CH:28][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]4[C:26]([CH3:27])=[CH:25][NH:24][C:21]4=[N:22][CH:23]=3)[S:17][C:13]=2[C:12]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH2:40]1COCC1.CO>>[CH3:40][C@:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([C:11]1[C:29]([CH3:30])=[CH:28][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]4[C:26]([CH3:27])=[CH:25][NH:24][C:21]4=[N:22][CH:23]=3)[S:17][C:13]=2[C:12]=1[C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C:7]([OH:9])=[O:8]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 21899815MeOH tetrahydrofuran

HCID 86699819HCID 86699819, compound

Product 1

HCID 86699818HCID 86699818, compound

Conditions

Temperature: 50 °C

Procedure

To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate: (8 mg, 0.015 mmol) in THF/CH3OH (0.5 mL/0.5 mL) was added 2N NaOH (75 μL, 0.15 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 C28H26ClN3O3S: 520.14 (M+H+); Found: 520.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.86 (d, J=1 Hz, 1H), 8.57 (d, J=1 Hz, 1H), 7.84 (s, 1H), 7.71-7.26 (m, 5H), 5.26 (s, 1H), 2.62 (s, 3H), 2.36 (s, 3H), 0.94 (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-744100e9e19f4d4f802f0f81dff440c8
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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