Sodium Hydroxide → HCID 86700468, compound

HRID 879654Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:11]1[C:35]([CH3:36])=[CH:34][C:14]2[N:15]=[C:16]([C:18]3[N:23]=[C:22]4[C:24]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH: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:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=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:35]([CH3:36])=[CH:34][C:14]2[N:15]=[C:16]([C:18]3[N:23]=[C:22]4[C:24]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH: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:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=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-(pyridin-3-yl)-1H-pyrazolo[4,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate (6 mg, 0.01 mmol) in THF (0.5 mL) and MeOH (0.5 mL) was added 2N NaOH (100 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 (3 mg). 1H NMR (400 MHz, CD3OD) δ 9.70 (bs, 1H), 8.97 (d, J=3.8 Hz, 1H), 8.60 (bs, 1H), 8.37 (d, J=4.4 Hz, 1H), 8.14 (d, J=4.2 Hz, 1H), 7.84-7.56 (m, 6H), 5.24 (s, 1H), 4.13 (s, 3H), 2.63 (s, 3H), 0.98 (s, 9H). LCMS-ESI+: calc'd for C32H28ClN5O3S: 598.2 (M+H+); Found: 598.2 (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)

Sources & evidence

ORD record: ord-52b7f7a32dd446768c13663991b8335d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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