1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (NE)-N-[[(8-bromo-4,5-dihydrothieno[3,2-d][1]benzoxepine-2-carbonyl)amino]-methylsulfanylmethylidene]carbamate

HRID 2385984노트

반응식

HRID 2385984 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([OH:17])=O)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:18]=1.CCN=C=NCCCN(C)C.[C:30]([NH:37][C:38](=[NH:41])[S:39][CH3:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([N:41]=[C:38]([S:39][CH3:40])[NH:37][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])=[O:17])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:18]=1

참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 579001638-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylic acidHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

생성물 1

HCID 178503937tert-butyl (NE)-N-[[(8-bromo-4,5-dihydrothieno[3,2-d][1]benzoxepine-2-carbonyl)amino]-methylsulfanylmethylidene]carbamate수율 67.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylic acid (10.0 g, 30.3 mmol), EDCI (7.5 g, 36.4 mmol) in DCM (200 mL) was stirred at room temperature for 10 min, then DMAP (7.39 g, 60.6 mmol) was added by one portion. 10 minutes later, N-Boc-2-Methyl-isothiourea (6.9 g, 36.4 mmol) was added. The reaction mixture was stirred at room temperature overnight. After removal of the solvent, the residue was treated with methanol/water (20 mL, 1:1) to afford 10.2 g of methyl N′-8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonyl-N-Boc-carbamimidothioate. Yield: 67%. 1H NMR (CDCl3, 400 MHz): δ12.33 (s, 1H), 7.95-7.51 (m, 2H), 7.35-6.94 (m, 2H), 4.28-4.25 (m, 2H), 3.15-3.30 (m, 2H), 2.52 (s, 3H), 1.51-1.45 (s, 9H). LC-MS: m/z=497 [M+H+]

후처리

  1. customAfter removal of the solvent
  2. additionthe residue was treated with methanol/water (20 mL, 1:1)

출처 및 근거

ORD 기록
ord-6f2892f0641a4e85a8aac8595dbc8bd1
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263633B2

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