3-Aminobenzamide → 3-[4-(3-Cyano-4-pyrrolidin-1-yl-phenyl)-pyrimidin-2-ylamino]-benzamide

HRID 1852408Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

5-(2-Chloro-pyrimidin-4-yl)-2-pyrrolidin-1-yl-benzonitrile (50 mg, 0.18 mmol) was dissolved in NMP (1 mL). 3-Aminobenzamide (100 mg, 0.734 mmol) was added and the mixture was heated at 140° C. in the microwave (300 W, stirring) for 45 minutes. The solvent was evaporated in vacuo (Genevac™). The residue was dissolved in DMSO (1.5 mL) and the crude product purified by reversed phase preparative LC-MS. Fractions containing desired product were combined and the solvents evaporated in vacuo (Genevac™). The title compound was afforded as an off-white solid (15.3 mg, 23%); LC-MS, Rt=8.00 min (ANALpH2_MeOH_QC), m/z 400 (MH+).

Workup

customThe solvent was evaporated in vacuo (Genevac™)
dissolutionThe residue was dissolved in DMSO (1.5 mL)
customthe crude product purified by reversed phase preparative LC-MS
additionFractions containing desired product
customthe solvents evaporated in vacuo (Genevac™)

Sources & evidence

ORD record: ord-36ea81b31c9c4e5cb7507af02dadb2d0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962609B2

Reaction notes

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