1-Hydroxybenzotriazole → N-Methyl-N-[3-(dimethylamino)propyl]-10-[(3-methoxy-2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2215128ノート

反応式

HRID 2215128 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:6]=[CH:7][C:8]=1[C:9]([N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][N:14]2[C:22]([C:25]([OH:27])=O)=[CH:23][CH:24]=[C:13]2[CH2:12]1)=[O:10].ON1C2C=CC=CC=2N=N1.Cl.[CH3:46][N:47]([CH3:56])[CH2:48][CH2:49][CH2:50][N:51]=[C:52]=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:52][N:51]([CH2:50][CH2:49][CH2:48][N:47]([CH3:56])[CH3:46])[C:25]([C:22]1[N:14]2[C:13]([CH2:12][N:11]([C:9]([C:8]3[CH:7]=[CH:6][C:5]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[CH:4][C:3]=3[O:2][CH3:1])=[O:10])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15]2)=[CH:24][CH:23]=1)=[O:27]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1027581410-[(3-Methoxy-2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid

生成物 1

HCID 10231007N-Methyl-N-[3-(dimethylamino)propyl]-10-[(3-methoxy-2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide収率 74.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 10-[(3-methoxy-2′-methyl[1,1′-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Example 10, Step F (0.40 g, 0.88 mmol), 3-(dimethylaminopropyl)-1-methyl amine (0.16 mL, 1.09 mmol) and 1-hydroxybenzotriazole (0.135 g, 0.96 mmol) in N,N-dimethylformamide (4 mL) was added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.19 g, 1.09 mmol) followed by N,N-diisopropylethyl amine (0.24 mL, 1.35 mmol). The reaction mixture was stirred overnight, then diluted with ethyl acetate and washed with water and saturated aqueous sodium bicarbonate. The organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow foam. Purification by flash chromatography on silica gel using a solvent system of 5% methanol in dichloromethane afforded 0.36 g of title compound as a white foam.

後処理

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow foam
  6. customPurification by flash chromatography on silica gel using a solvent system of 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-2457ea9acb34468f96a10e2675e3ab1c
出典データセット
uspto-grants-2006_09
特許番号
US07109193B2

反応ノート

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