Sodium Hydroxide → HCID 86700458, compound

HRID 879646Notes

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]=[N:20][C:21]([CH3:34])=[C:22]([C:24]4[N:29]=[C:28]5[CH:30]=[N:31][N:32]([CH3:33])[C:27]5=[CH:26][CH:25]=4)[CH:23]=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+]>C1COCC1.CO>[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]=[N:20][C:21]([CH3:34])=[C:22]([C:24]4[N:29]=[C:28]5[CH:30]=[N:31][N:32]([CH3:33])[C:27]5=[CH:26][CH:25]=4)[CH:23]=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])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(6-methyl-5-(1-methyl-1H-pyrazolo[4,3-b]pyridin-5-yl)pyridin-3-yl)benzo[d]thiazol-6-yl)acetate (26 mg, 0.042 mmol) in THF (0.5 mL) and MeOH (0.5 mL) was added 2N NaOH (410 μL). The reaction mixture was heated at 60° C. for 3 h. The reaction mixture was concentrated down, the residue was dissolved in DMF and MeOH, filtered and purified by reverse phase HPLC, (10-100% ACN/H2O+0.1% TFA) to give the product. 1H NMR (400 MHz, CD3OD) δ 9.11 (d, J=0.8 Hz, 1H), 8.59 (d, J=1.0 Hz, 1H), 8.22-8.18 (m, 2H), 7.81 (s, 1H), 7.69-7.62 (m, 2H), 7.53-7.51 (m, 3H), 5.23 (s, 1H), 4.15 (s, 3H), 2.67 (s, 3H), 2.57 (s, 1H), 0.95 (s, 9H). LCMS-ESI+: calc'd for C33H30ClN5O3S: 612.2 (M+H+); Found: 612.1 (M+H+).

Workup

concentrationThe reaction mixture was concentrated down
dissolutionthe residue was dissolved in DMF
filtrationMeOH, filtered
custompurified by reverse phase HPLC, (10-100% ACN/H2O+0.1% TFA)
customto give the product

Sources & evidence

ORD record: ord-173417cefc3442359967254cb0821b51
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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