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 400488노트

반응식

HRID 400488 반응식
[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

참가 물질

7

반응물 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

생성물 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]-ethanone수율 52.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-134a8977589c4316960f7636866a73ff
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741892B2

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