Sodium Hydroxide → HCID 86700464, compound

HRID 879649Notes

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[N:23]=[C:22]4[C:24]([N:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)=[N:25][N:26]([CH3:27])[C:21]4=[CH:20][CH:19]=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[N:23]=[C:22]4[C:24]([N:28]5[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]5)=[N:25][N:26]([CH3:27])[C:21]4=[CH:20][CH:19]=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: 45 °C

Procedure

To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(4-methylpiperazin-1-yl)-1H-pyrazolo[4,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate (11 mg, 0.017 mmol) in THF (0.5 mL) and MeOH (0.5 mL) was added 2N NaOH (174 μL). The reaction mixture was heated at 45° C. overnight. The reaction mixture was concentrated, 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 8.33 (d, J=4.4 Hz, 1H), 7.97 (d, J=4.4 Hz, 1H), 7.85 (s, 1H), 7.70-7.57 (m, 4H), 5.22 (s, 1H), 4.75-4.74 (m, 2H), 3.92 (s, 3H), 3.61-3.59 (m, 2H), 3.36-3.34 (m, 4H), 2.94 (s, 3H), 2.61 (s, 3H), 0.96 (s, 9H). .LCMS-ESI+: calc'd for C32H35ClN6O3S: 619.2 (M+H+); Found: 619.3 (M+H+).

Workup

concentrationThe reaction mixture was concentrated
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-cf37ea9eb88141f3a8b21c8cb9e60be7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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