Piperidine-1-propylamine → N-(2-aminophenyl)-4-{2-[(3-piperidin-1-ylpropyl)amino]pyrimidin-5-yl}benzamide

HRID 888031Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[N:25][C:26](Cl)=[N:27][CH:28]=2)=[CH:19][CH:18]=1)=O)(C)(C)C.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C)C(=O)C>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[N:27][C:26]([NH:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[N:25][CH:24]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2-t-butoxycarbonylaminophenyl)-4-(2-chloropyrimidin-5-yl)benzamide (Method 53, 80 mg, 0.19 mmol) in N,N-dimethylacetamide (3.5 ml) was added 3-aminopropylpiperidine (108 mg 0.76 mmol). The reaction mixture was stirred at 50° C. for 20 hours, before being allowed to cool. The reaction mixture was partitioned between water and ethyl acetate, before being filtered under gravity, through a Varian Chem Elut (CE1010) diatomaceous earth column. The resulting solution was then concentrated under reduced pressure and purified by flash column chromatography, eluting with methanol/dichloromethane (0-20%), to give the title compound, which was used without further purification; Mass Spectrum: M+H+ 531.

Workup

temperatureto cool
customThe reaction mixture was partitioned between water and ethyl acetate
filtrationbefore being filtered under gravity, through a Varian Chem Elut (CE1010) diatomaceous earth column
concentrationThe resulting solution was then concentrated under reduced pressure
custompurified by flash column chromatography
washeluting with methanol/dichloromethane (0-20%)

Sources & evidence

ORD record: ord-6df7dee80a4e48a483460eaf080c52b2
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247562B2

Reaction notes

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