Acetylglycine → (E)-2-acetamido-4'-benzylthio-3'-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]acetanilide dihydrochloride

HRID 48331

반응식

HRID 48331 반응식
[ClH:1].Cl.[CH2:3]([S:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1/[CH:18]=[CH:19]/[C:20]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]([CH3:31])[CH2:23][CH2:22][N:21]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:32]([NH:35][CH2:36][C:37](O)=[O:38])(=[O:34])[CH3:33].ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[ClH:1].[ClH:1].[C:32]([NH:35][CH2:36][C:37]([NH:15][C:14]1[CH:16]=[CH:17][C:11]([S:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:12](/[CH:18]=[CH:19]/[C:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]([CH3:31])[CH2:23][CH2:22][N:21]=2)[CH:13]=1)=[O:38])(=[O:34])[CH3:33]

참가 물질

6

반응물 4

HCID 10972AcetylglycineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22742398(E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride

생성물 1

HCID 22742245(E)-2-acetamido-4'-benzylthio-3'-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]acetanilide dihydrochloride수율 30.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 58 mg (0.114 mmol) of (E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride (prepared as described in Example 82), 20 mg (0.171 mmol) of N-acetylglycine and 1-hydroxy-7-azabenzotriazole in 5 ml of dimethylformamide was added 44 mg (0.228 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The mixture was stirred for 4 hours. The solvent was removed and the residue was purified by column chromatography eluting with 5-20% methanol/dichloromethane and treated with 0.10 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated and the residue was recrystallised from acetone/methanol/diethyl ether to give 10 mg of (E)-2-acetamido-4′-benzylthio-3′-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]acetanilide dihydrochloride as a yellow solid; MS: m/e 499 (M+).

후처리

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography
  3. washeluting with 5-20% methanol/dichloromethane
  4. additiontreated with 0.10 ml of 4M hydrogen chloride in dioxan
  5. customThe solvent was evaporated
  6. customthe residue was recrystallised from acetone/methanol/diethyl ether

출처 및 근거

ORD 기록
ord-0846c4213df5443fbb8ab065be09d321
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703387B2

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