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Dimethylformamide → N-(2-Amino-1-cyano-2-oxoethyl)-5-chloro-6-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]pyridine-3-carboxamide

HRID 2414339
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인쇄 미리보기

반응식

HRID 2414339 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:25](O)=[O:26])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][O:16][C:15]2=[O:24])[CH2:10][CH2:9]1.C(Cl)(=O)C(Cl)=O.C[N:35](C)[CH:36]=[O:37].C([N:42](CC)[CH:43]([CH3:45])C)(C)C.C[N:49]1CCCC1=O>ClCCl>[NH2:35][C:36](=[O:37])[CH:45]([NH:49][C:25]([C:4]1[CH:5]=[N:6][C:7]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][O:16][C:15]3=[O:24])[CH2:10][CH2:9]2)=[C:2]([Cl:1])[CH:3]=1)=[O:26])[C:43]#[N:42]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 13387N-methyl-2-pyrrolidoneHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 226445845-Chloro-6-[4-(2-oxo-2h-3,1-benzoxazin-1(4h)-yl)piperidin-1-yl]pyridine-3-carboxylic acid

생성물 1

HCID 22644626
N-(2-Amino-1-cyano-2-oxoethyl)-5-chloro-6-[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]pyridine-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The product of example 148 step (i) (0.14 g) was stirred as a suspension in dichloromethane (4 ml) and to this mixture was added oxalyl chloride (0.05 g) followed by N,N-dimethylformamide (0.01 g). After stirring for 1 h at room temperature the mixture was treated with 2-aminocyanoacetanide (0.14 g) 1-methyl-2-pyrrolidinone (3 ml) and then N,N-diisopropylethylamine (1 ml), stirring was then continued for a further 18 h at room temperature. The reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate, the organic layer was washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 25% ethyl acetate/isohexane. Yield 0.09 g as a solid.

후처리

  1. waitwas then continued for a further 18 h at room temperature
  2. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 25% ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-e81565842d6f45cb973086b00fe0a1d1
출처 데이터셋
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06812226B2

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