N-methyl-2-pyrrolidone → N-(2-methyl-1,3-benzothiazol-5-yl)-2-((7H-pyrrolo[2,3-d]pyrimidin-4-ylmethyl)amino)-3-pyridinecarboxamide

HRID 888164Notes

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].Cl.Cl.[N:23]1[C:28]2[NH:29][CH:30]=[CH:31][C:27]=2[C:26]([CH2:32][NH2:33])=[N:25][CH:24]=1.CCN(C(C)C)C(C)C.CN1C(=O)CCC1>CC(O)(C)C.CCOC(C)=O>[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:33][CH2:32][C:26]4[C:27]5[CH:31]=[CH:30][NH:29][C:28]=5[N:23]=[CH:24][N:25]=4)=[N:20][CH:19]=[CH:18][CH:17]=3)=[O:5])=[CH:16][C:11]=2[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Fluoro-N-(2-methyl-benzothiazol-5-yl)-nicotinamide (109 mg, 0.38 mmol) was dissolved in t-BuOH (1 mL), then added C-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-methylamine dihydrochloride (126 mg, 0.57 mmol) and DIEA (132 μL, 0.76 mmol). The reaction was heated at 100° C. for 21 h. The t-BuOH was replaced with NMP (0.5 mL), then additional C-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-methylamine dihydrochloride (42 mg, 0.19 mmol) and DIEA (0.15 mL, 0.874 mmol) were added and the mixture was heated at 120° C. for another 21 h. The mixture was diluted with EtOAc. A precipitate formed and was collected by decanting off the EtOAc. Purification was achieved by preparative TLC (10% MeOH/CH2Cl2) to give N-(2-methyl-1,3-benzothiazol-5-yl)-2-((7H-pyrrolo[2,3-d]pyrimidin-4-ylmethyl)amino)-3-pyridinecarboxamide as a light yellow solid. MS m/e 416.1 (M+H)+ Calc'd for C21H17N7OS—415.4.

Workup

temperaturethe mixture was heated at 120° C. for another 21 h
customA precipitate formed
customwas collected
customby decanting off the EtOAc
customPurification

Sources & evidence

ORD record: ord-b15a300cd17e4831b17550f5c77fa6fe
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247556B2

Reaction notes

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