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

HRID 400488ノート

反応式

HRID 400488 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH: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.[S:34]1[C:43]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38][C:37]=2[N:36]=[C:35]1[NH2:44].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[NH2:44][C:35]1[S:34][C:43]2[CH2:42][CH2:41][N:40]([C:21](=[O:22])[CH2:20][N:10]3[C:11]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)=[CH:12][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9]3)[CH2:39][CH2:38][C:37]=2[N:36]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 866860295,6,7,8-tetrahydro-4H-Thiazolo[4,5-d]azepin-2-amine hydrobromideHCID 86686085(3,5-Bis-(4-fluoro-phenyl)-pyrazol-1-yl)-acetic acid

生成物 1

HCID 715865471-(2-Amino-4,5,7,8-tetrahydro-thiazolo (4,5-d) azepin-6-yl)-2-[3,5-bis-(4-fluoro-phenyl)-pyrazol-1-yl]-ethanone収率 52.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

100 mg (3,5-bis-(4-fluoro-phenyl)-pyrazol-1-yl)-acetic acid was dissolved in 2 mL DMF. 165 mg PFTU and 170 μL DIPEA were added to this solution and the mixture was stirred for 15 min at RT. Then, 160 mg 5,6,7,8-Tetrahydro-4H-thiazolo (4,5-d) azepin-2-ylamine hydrobromide was added and the reaction was stirred over night. Then, K2CO3 solution (5%) and CH2Cl2 were added, the organic phase was separated and washed two times with water. The solvent was removed and the residue was purified by HPLC (method 1) to give 78 mg of the desired compound. Rt: 0.80 min (method C), (M+H)+: 466

後処理

  1. stirringthe reaction was stirred over night
  2. customthe organic phase was separated
  3. washwashed two times with water
  4. customThe solvent was removed
  5. customthe residue was purified by HPLC (method 1)

出典と根拠

ORDレコード
ord-134a8977589c4316960f7636866a73ff
出典データセット
uspto-grants-2014_06
特許番号
US08741892B2

反応ノート

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