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Sodium Bicarbonate → (S,E)-2-((4-cyanophenyl)amino)-N-(3-(2-(4-(dimethylamino)-N-methyl-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide

HRID 2284695
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HRID 2284695 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:35])[C@@H:31]([NH:33][CH3:34])[CH3:32])[CH:24]=3)=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:37][N:38]([CH3:45])[CH2:39]/[CH:40]=[CH:41]/[C:42](O)=[O:43].Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)C(C)C)(C)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:35])[C@@H:31]([N:33]([CH3:34])[C:42](=[O:43])/[CH:41]=[CH:40]/[CH2:39][N:38]([CH3:45])[CH3:37])[CH3:32])[CH:24]=3)=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2]
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참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 90053313(S)-2-((4-cyanophenyl)amino)-N-(3-(2-(methylamino)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide

생성물 1

HCID 117857077
(S,E)-2-((4-cyanophenyl)amino)-N-(3-(2-(4-(dimethylamino)-N-methyl-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide
수율 57.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 81531Diisopropylethylamine용매

실험 절차

To a solution of (S)-2-((4-cyanophenyl)amino)-N-(3-(2-(methylamino)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide (E1) dihydrochloride (58 mg), 4-dimethylaminocrotonic acid hydrochloride (33 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg) in N,N-dimethylformamide (1 mL), N,N-diisopropylethylamine (174 μL) was added at room temperature, and the mixture was stirred at the same temperature for 15 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate was added. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure. The obtained solid matter was purified by basic silica gel column chromatography (eluent, 98 to 88% ethyl acetate in methanol) to obtain (S,E)-2-((4-cyanophenyl)amino)-N-(3-(2-(4-(dimethylamino)-N-methyl-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide (6-1, 41 mg) as white solid.

후처리

  1. filtrationThe solid matter was taken by filtration
  2. washwashed with water
  3. customdried under reduced pressure
  4. customThe obtained solid matter was purified by basic silica gel column chromatography (eluent, 98 to 88% ethyl acetate in methanol)

출처 및 근거

ORD 기록
ord-79c3043f1ef543148e543112e274fc24
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145415B2

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