Cesium carbonate → 4-(3-(1H-imidazol-1-yl)benzylamino)-6-(4-(dimethylcarbamoyl)phenylamino)nicotinamide

HRID 513282ノート

反応式

HRID 513282 の反応式
[N:1]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[CH2:9][NH:10][C:11]2[C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=[C:13](Cl)[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:1]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[CH2:9][NH:10][C:11]2[C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=[C:13]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([C:29](=[O:30])[N:31]([CH3:32])[CH3:33])=[CH:34][CH:35]=3)[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 2355274-Amino-N,N-dimethylbenzamideHCID 634876Binap, (A+-)-HCID 866645474-(3-(1H-imidazol-1-yl)benzylamino)-6-chloronicotinamide

生成物 1

HCID 569684754-(3-(1H-imidazol-1-yl)benzylamino)-6-(4-(dimethylcarbamoyl)phenylamino)nicotinamide収率 9%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 4-(3-(1H-imidazol-1-yl)benzylamino)-6-chloronicotinamide (56 mg, 0.170 mmol), 4-amino-N,N-dimethylbenzamide (42 mg, 0.256 mmol), Cs2CO3 (110 mg, 0.337 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 120 C for 3 h. The mixture was concentrated in vacuo, the residue was purified by HPLC to give the titled compound (7 mg). MS 456.3 (M+H); UV 257.8 nm; t 0.344 min.

後処理

  1. customwas degassed with Ar
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by HPLC

出典と根拠

ORDレコード
ord-605737e9bf7a4f22bc07d5b40639400e
出典データセット
uspto-grants-2015_08
特許番号
US09102625B2

反応ノート

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