Water → HCID 71534822, compound

HRID 521212Notes

Reaction equation

C1CCN2C(=NCCC2)CC1.[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:27]([C:28]([NH2:30])=[O:29])=[CH:26][NH:25][N:24]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14].[C:31]([CH:33]=[C:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1)#[N:32].O>CN(C=O)C>[C:28]([C:27]1[C:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([S:13]([CH3:12])(=[O:14])=[O:15])=[CH:21][CH:20]=2)=[N:24][N:25]([C:34]2([CH2:33][C:31]#[N:32])[CH2:35][CH2:36][N:37]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:38][CH2:39]2)[CH:26]=1)(=[O:29])[NH2:30]

Participants

Conditions

Temperature: 50 °C

Procedure

DBU (0.118 mL, 0.785 mmol) was added 3-((4-(methylsulfonyl)phenyl)amino)-1H-pyrazole-4-carboxamide (Intermediate 34-2) (200 mg, 0.714 mmol) and tert-butyl 4-(cyanomethylidene)piperidine-1-carboxylate (Intermediate 19-1) (317 mg, 1.43 mmol) stirred in DMF (3 mL) and the mixture was heated to 50° C. for 5 h. The reaction mixture was cooled to 23° C., water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The combined organic fractions were dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with EtOAc/hexanes to afford the title compound.

Workup

temperatureThe reaction mixture was cooled to 23° C.
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic fractions were dried (Na2SO4)
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel eluting with EtOAc/hexanes

Sources & evidence

ORD record: ord-b6d1a1b0d0df4715ba0ba077701abab8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328099B2

Reaction notes

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