Water → ethyl 5-chloro-6-{[(3R)-1-(4-fluorobenzyl)-3-pyrrolidinyl]amino}nicotinate

HRID 2376026노트

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HRID 2376026 반응식
Cl.Cl.[F:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][C@@H:11]([NH2:14])[CH2:10]2)=[CH:6][CH:5]=1.[CH2:17]([O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[C:24](Cl)=[N:23][CH:22]=1)[CH3:18].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Cl:27][C:25]1[C:24]([NH:14][C@@H:11]2[CH2:12][CH2:13][N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:16][CH:15]=3)[CH2:10]2)=[N:23][CH:22]=[C:21]([CH:26]=1)[C:20]([O:19][CH2:17][CH3:18])=[O:29]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16762519Ethyl 5,6-DichloronicotinateHCID 53256257HCID 53256257, 화합물

생성물 1

HCID 68962258ethyl 5-chloro-6-{[(3R)-1-(4-fluorobenzyl)-3-pyrrolidinyl]amino}nicotinate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of (3R)-1-(4-fluorobenzyl)-3-pyrrolidinamine dihydrochloride (3.5 g) in DMF (35 ml) was added 5,6-dichloronicotinic acid ethyl ester (3.38 ml) and K2CO3 (6.34 g), the mixture was stirred at 100° C. for 4 hours under N2 atmosphere. The mixed solution was poured into a mixture of water (250 ml) and AcOEt (250 ml). The organic layer was separated, washed with water twice and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt:hexane=1:2 to give ethyl 5-chloro-6-{[(3R)-1-(4-fluorobenzyl)-3-pyrrolidinyl]amino}nicotinate (3.75 g).

후처리

  1. customThe organic layer was separated
  2. washwashed with water twice
  3. dry with materialbrine, dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with AcOEt

출처 및 근거

ORD 기록
ord-037271096e8f4c6dbab4c2b479de9b30
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465731B2

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