Diisopropylethylamine → N-(2-methyl-1,3-benzothiazol-5-yl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide

HRID 888162Notes

Reaction equation

F[C:2]1[N:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([CH3:15])=[N:12][C:11]=2[CH:16]=1)=[O:5].[NH:21]1[C:25]2=[N:26][CH:27]=[CH:28][C:29]([CH2:30][NH2:31])=[C:24]2[CH:23]=[N:22]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:15][C:13]1[S:14][C:10]2[CH:9]=[CH:8][C:7]([NH:6][C:4]([C:3]3[C:2]([NH:31][CH2:30][C:29]4[CH:28]=[CH:27][N:26]=[C:25]5[NH:21][N:22]=[CH:23][C:24]=45)=[N:20][CH:19]=[CH:18][CH:17]=3)=[O:5])=[CH:16][C:11]=2[N:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-Fluoro-N-(2-methyl-benzothiazol-5-yl)-nicotinamide (100 mg, 0.348 mmol) was dissolved in NMP (0.5 mL), then C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (52 mg, 0.348 mmol) and DIEA (91 μL, 0.522 mmol) were added. The reaction was heated at 120° C. for 20 h. Additional C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (25 mg, 0.174 mmol) and DIEA (91 μL, 0.522 mmol) were added and the mixture was heated at 120° C. for another 23 h. The mixture was partitioned between H2O and EtOAc then extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. Purification was achieved by preparative TLC (10% MeOH/CH2Cl2), followed by trituration with CH2Cl2 to give N-(2-methyl-1,3-benzothiazol-5-yl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide as a light yellow solid. MS m/e 416.0 (M+H)+. Calc'd for C21H17N7O—415.48.

Workup

temperaturethe mixture was heated at 120° C. for another 23 h
customThe mixture was partitioned between H2O and EtOAc
extractionthen extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
customPurification

Sources & evidence

ORD record: ord-f9307c2639e94ad18fd5fe1bd9da839b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247556B2

Reaction notes

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