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

HRID 2376026ノート

反応式

HRID 2376026 の反応式
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]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16762519Ethyl 5,6-DichloronicotinateHCID 53256257HCID 53256257、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-037271096e8f4c6dbab4c2b479de9b30
出典データセット
uspto-grants-2008_12
特許番号
US07465731B2

反応ノート

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