Sodium Hydroxide → 2-methyl-2-(5-methyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl)propan-1-amine

HRID 44676Notes

Reaction equation

[CH3:1][C:2]([C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][N:27]=[CH:28][C:21]=23)[S:17][C:18]=1[CH3:19])([CH3:13])[CH2:3][NH:4]C(=O)C1C=CC=CC=1.[OH-].[Na+]>CCO>[CH3:13][C:2]([C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][N:27]=[CH:28][C:21]=23)[S:17][C:18]=1[CH3:19])([CH3:1])[CH2:3][NH2:4]

Participants

Conditions

Temperature: 170 °C

Procedure

N-[2-methyl-2-[5-methyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl]propyl]benzamide (55 mg, 0.1405 mmol) was dissolved in EtOH (1 mL) and treated with 5M NaOH (2.5 mL). The reaction was heated at 170° C. in the microwave for 500 minutes. The mixture was extracted with EtOAc followed by DCM and the combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (70:9:1, DCM/MeOH/NH4OH) to give the required product as a pale lemon solid (18.9 mg, 47% Yield). 1H NMR (DMSO, 400 MHz) δ 1.40 (6H, s), 2.61 (3H, s), 2.88 (2H, s), 7.51 (1H, s), 8.56 (2H, m); MS (ES+) 288.00

Workup

extractionThe mixture was extracted with EtOAc
dry with materialthe combined organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (70:9:1, DCM/MeOH/NH4OH)

Sources & evidence

ORD record: ord-2f3f310d033442ff98474ce85ccae493
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541445B2

Reaction notes

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