Cumylamine → ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate

HRID 448131ノート

反応式

HRID 448131 の反応式
[C:1]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH2:34]([O:36][C:37]([N:39]1[C:43]2[S:44][C:45]([C:47](O)=[O:48])=[CH:46][C:42]=2[C:41]([NH:50][C:51](=[O:64])[C:52]2[CH:57]=[CH:56][C:55]([N:58]3[CH2:63][CH2:62][O:61][CH2:60][CH2:59]3)=[CH:54][CH:53]=2)=[N:40]1)=[O:38])[CH3:35].CCN(C(C)C)C(C)C>CN(C)C=O.O>[CH3:2][C:1]([NH:10][C:47]([C:45]1[S:44][C:43]2[N:39]([C:37]([O:36][CH2:34][CH3:35])=[O:38])[N:40]=[C:41]([NH:50][C:51](=[O:64])[C:52]3[CH:57]=[CH:56][C:55]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)=[CH:54][CH:53]=3)[C:42]=2[CH:46]=1)=[O:48])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3]

参加物

7

反応物 4

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667857921-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride

生成物 1

HCID 44520544ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate収率 93.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of cumylamine (1.43 g, 10.6 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 3.40 g, 10.6 mmol), 1-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride (3.40 mg, 7.07 mmol) and N,N′-diisopropylethylamine (12.1 mL, 7.07 mmol) in 80 mL of dimethylformamide was stirred at room temperature for 20 hours. Afterward the reaction mixture was diluted with water and extracted with dichloromethane. Volatiles were removed by evaporation under reduced pressure and the residue was triturated with ethyl acetate, filtered, extensively washed with diethyl ether and dried under vacuum at 40° C., to give 3.7 g of the title compound, used in the next step without further purification.

後処理

  1. extractionextracted with dichloromethane
  2. customVolatiles were removed by evaporation under reduced pressure
  3. customthe residue was triturated with ethyl acetate
  4. filtrationfiltered
  5. washextensively washed with diethyl ether
  6. customdried under vacuum at 40° C.

出典と根拠

ORDレコード
ord-29db0bf3015440778be39bfe1ff617d1
出典データセット
uspto-grants-2013_07
特許番号
US08481584B2

反応ノート

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