Diisopropylethylamine → 1-(2-Amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-2-(3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-ethanone

HRID 239193ノート

反応式

HRID 239193 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Br.Br.[S:35]1[C:44]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39][C:38]=2[N:37]=[C:36]1[NH2:45].C(=O)([O-])O.[Na+]>CN(C=O)C.C(Cl)Cl>[NH2:45][C:36]1[S:35][C:44]2[CH2:43][CH2:42][N:41]([C:21](=[O:22])[CH2:20][N:10]3[C:11]([C:13]4[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=4)=[N:12][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[N:9]3)[CH2:40][CH2:39][C:38]=2[N:37]=1

参加物

7

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 516892Sodium BicarbonateHCID 199857845,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-ylamine dihydrobromideHCID 86686517(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid

生成物 1

HCID 866865231-(2-Amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-2-(3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-ethanone収率 53.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

350 mg (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid and 0.2 mL DIPEA were dissolved in 4.5 mL DMF. 570 mg PFTU was added to this solution and the mixture was stirred for 7 min at RT. Then, 333 mg 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-ylamine dihydrobromide and 0.4 mL DIPEA were added and the reaction was stirred over night at RT. Then, sodium hydrogencarbonate solution (10%) and CH2Cl2 were added, the organic phase was separated and the solvent was removed. The residue was purified by HPLC to yield 252 mg of the desired compound.

後処理

  1. addition570 mg PFTU was added to this solution
  2. stirringthe reaction was stirred over night at RT
  3. customthe organic phase was separated
  4. customthe solvent was removed
  5. customThe residue was purified by HPLC

出典と根拠

ORDレコード
ord-84a199eadd7a445f89b07b5e7c50674a
出典データセット
uspto-grants-2014_02
特許番号
US08642774B2

反応ノート

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