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Potassium Carbonate → (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-1-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-piperazin-1-yl]-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butan-1,4-dione

HRID 736944
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인쇄 미리보기

반응식

HRID 736944 반응식
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH2:6]2.[NH2:16][C:17]1[C:48]([C:49]([F:52])([F:51])[F:50])=[CH:47][C:20]([CH2:21][C@@H:22]([CH2:26][C:27](=[O:46])[N:28]2[CH2:33][CH2:32][CH:31]([N:34]3[CH2:40][CH2:39][C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[NH:36][C:35]3=[O:45])[CH2:30][CH2:29]2)[C:23](O)=[O:24])=[CH:19][C:18]=1[Cl:53].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:16][C:17]1[C:48]([C:49]([F:51])([F:50])[F:52])=[CH:47][C:20]([CH2:21][C@@H:22]([CH2:26][C:27]([N:28]2[CH2:33][CH2:32][CH:31]([N:34]3[CH2:40][CH2:39][C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[NH:36][C:35]3=[O:45])[CH2:30][CH2:29]2)=[O:46])[C:23]([N:13]2[CH2:14][CH2:15][N:10]([CH:5]3[CH2:6][CH:7]4[N:2]([CH3:1])[CH:3]([CH2:9][CH2:8]4)[CH2:4]3)[CH2:11][CH2:12]2)=[O:24])=[CH:19][C:18]=1[Cl:53]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 154797638-Methyl-3-(piperazin-1-yl)-8-azabicyclo[3.2.1]octaneHCID 68591515(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoic acid

생성물 1

HCID 57848362(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-1-[4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-piperazin-1-yl]-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butan-1,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

850 mg (2.4 mmol) 8-methyl-3-piperazin-1-yl-8-aza-bicyclo[3.2.1]octan were added to a solution of 1.04 g (1.88 mmol) (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoic acid, 642 mg (2.0 mmol) TBTU and 1.64 mL (9.6 mmol) ethyldiisopropylamine in 20 mL DMF and the reaction mixture was stirred overnight at RT. The reaction solution was combined with 15% K2CO3 solution, stirred for 10 min at RT, the precipitated substance was suction filtered, washed with 50 mL water and dried in the air and purified by chromatography (silica gel, gradient: DCM to DCM/MeOH/NH3 10:85:5).

후처리

  1. stirringstirred for 10 min at RT
  2. filtrationfiltered
  3. washwashed with 50 mL water
  4. customdried in the air
  5. custompurified by chromatography (silica gel, gradient: DCM to DCM/MeOH/NH3 10:85:5)

출처 및 근거

ORD 기록
ord-c956c973a81b48c2b944cc644a99fbc9
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595312B2

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