Triethylamine → 10-{[6-Chloro-3-methoxy-2'-ethoxy-[1,1'-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2184470노트

반응식

HRID 2184470 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH3:21].S(Cl)(Cl)=O.[CH:26]1[CH:27]=[CH:28][N:29]2[CH2:35][C:34]3[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=3[NH:32][CH2:31][C:30]=12.C(N(CC)CC)C>O1CCCC1.ClCCl.CN(C)C=O>[Cl:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][CH3:21])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8]([N:32]2[C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[CH2:35][N:29]3[CH:28]=[CH:27][CH:26]=[C:30]3[CH2:31]2)=[O:10])[CH:7]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 21947830HCID 21947830, 화합물

생성물 1

HCID 2194775610-{[6-Chloro-3-methoxy-2'-ethoxy-[1,1'-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of the 2-chloro-2′-ethoxy-5-methoxy[1,1′-biphenyl]-4-carboxylic acid of Step A (0.491 g) in tetrahydrofuran (5 mL) containing a catalytic amount of N,N-dimethylformamide was added dropwise thionyl chloride (0.210 g, 1.76 mmol). The reaction mixture was stirred for 2 hours, and then added dropwise to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.294 g, 1.60 mmol) in tetrahydrofuran (5 mL) containing triethylamine (0.357 g, 3.52 mmol). The reaction mixture was stirred for 2 hours, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. Trituration of the residue with methanol provided the title compound as an off-white solid, 99.24% pure by analytical HPLC [Primesphere C-18 column (2.0×150 mm); mobile phase 70/30 acetonitrile/water containing 0.1% phosphoric acid], m.p. 213-215° C.

후처리

  1. stirringThe reaction mixture was stirred for 2 hours
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-9be7f64ab1ff4490a6de31713bb85ac9
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900200B2

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