Methanol → 4-(Pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide

HRID 492958노트

반응식

HRID 492958 반응식
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1.CO>O1CCCC1.[C].[Pd]>[NH2:30][C:28]1[CH:27]=[CH:26][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:29]=1

참가 물질

5

반응물 2

HCID 887MethanolHCID 866021734-(Pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide

생성물 1

HCID 866021744-(Pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide수율 99.9%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

4-(Pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide (290 mg) was dissolved in tetrahydrofuran (7 ml) and methanol (7 ml) under a nitrogen atmosphere, and then 10% palladium carbon (139 mg) was added, followed by stirring under a hydrogen atmosphere for 10 hrs. The reaction mixture was filtered to remove the catalyst, and the catalyst was washed with methanol. The filtrate was concentrated to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate). Fractions containing a target compound were concentrated to provide a crude product of 4-(pyrrolidin-1-ylmethyl)piperidine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide (270 mg) as white foam.

후처리

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. washthe catalyst was washed with methanol
  4. concentrationThe filtrate was concentrated
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate)
  7. additionFractions containing a target compound
  8. concentrationwere concentrated

출처 및 근거

ORD 기록
ord-c14ca9084262489abef464a305110128
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

반응 노트

불러오는 중…