1-Methylpyrrolidine → HCID 118036082, compound

HRID 522744Notes

Reaction equation

Cl.[F:2][C:3]([CH3:8])([CH3:7])[CH2:4][CH2:5][NH2:6].CN1CCCC1.[F:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:23]2[CH:34]=[N:33][C:26]3[N:27]=[C:28]([NH:31][CH3:32])[N:29]=[CH:30][C:25]=3[CH:24]=2)=[CH:18][C:17]=1[NH:35][C:36](=O)[O:37]C(C)=C>O1CCOCC1>[F:2][C:3]([CH3:8])([CH3:7])[CH2:4][CH2:5][NH:6][C:36]([NH:35][C:17]1[CH:18]=[C:19]([C:23]2[CH:34]=[N:33][C:26]3[N:27]=[C:28]([NH:31][CH3:32])[N:29]=[CH:30][C:25]=3[CH:24]=2)[C:20]([CH3:22])=[CH:21][C:16]=1[F:15])=[O:37]

Participants

Conditions

Temperature: 80 °C

Procedure

Add 3-fluoro-3-methyl-butan-1-amine hydrochloride (88 mg, 0.62 mmol) followed by N-methylpyrrolidine (0.065 mL, 0.62 mmol) to a stirred solution of isopropenyl N-[2-fluoro-4-methyl-5-(2-methylaminopyrido[2,3-d]pyrimidin-6-yl)phenyl]carbamate (184 mg, 0.50 mmol) in 1,4-dioxane (5 mL) and heat at 80° C. under N2 overnight. Concentrate and purify on silica eluting with 0-5% MeOH (2N NH3)/DCM. Purify on SCX column eluting with NH3/MeOH to obtain the title compound (219 mg, 70%). MS (m/z): 414.8 (M+1).

Workup

concentrationConcentrate
custompurify on silica eluting with 0-5% MeOH (2N NH3)/DCM
customPurify on SCX column
washeluting with NH3/MeOH

Sources & evidence

ORD record: ord-7ca5735bf9e149a0a049cfa0a912f906
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334267B2

Reaction notes

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