(4-aminophenyl)(4-methylpiperazin-1-yl)methanone → HCID 44183499, compound

HRID 1966396Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([C:11]3[CH:16]=[C:15]([F:17])[C:14]([CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[C:13]([F:25])[CH:12]=3)[C:6]=2[N:7]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[O:34])=[CH:29][CH:28]=1.CC([O-])(C)C.[K+]>C1COCC1>[F:25][C:13]1[CH:12]=[C:11]([N:8]2[C:6]3[N:7]=[C:2]([NH:26][C:27]4[CH:28]=[CH:29][C:30]([C:33]([N:35]5[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]5)=[O:34])=[CH:31][CH:32]=4)[N:3]=[CH:4][C:5]=3[CH:10]=[CH:9]2)[CH:16]=[C:15]([F:17])[C:14]=1[CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a sealed tube, 2-chloro-7-(3,5-difluoro-4-morpholin-4-ylmethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine (50.0 mg, 0.130 mmol), (4-Amino-phenyl)-(4-methyl-piperazin-1-yl)-methanone (42.1 mg, 0.182 mmol), KOtBu (21.1 mg, 0.182 mmol) and SK-CC02-A (12.5 mg, 0.020 mmol, Pd catalyst 2-(Dimethylaminomethyl)-ferrocen-1-yl-palladium(II)-chlorid Dinorbornylphosphin Complex, Fluka No. 44696) are suspended in THF (2 ml) under Ar. The reaction mixture is stirred at 80° C. for 1.5 h, cooled to rt, and then filtered through a Celite plug. The filtrate is concentrated under reduce pressure. The residue is purified by reverse phase prep-HPLC (Waters) to afford the title compound (2) as a white solid. HPLC: tR=0.89 min (Method A); MS-ES: (M+H)+=548.

Workup

temperaturecooled to rt
filtrationfiltered through a Celite plug
concentrationThe filtrate is concentrated
customThe residue is purified by reverse phase prep-HPLC (Waters)

Sources & evidence

ORD record: ord-eefa320a3b1d47929f59bb691e0228ff
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420657B2

Reaction notes

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