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 708213ノート

反応式

HRID 708213 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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+]

後処理

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

出典と根拠

ORDレコード
ord-91876d429c434f8ea67305f631aadfc3
出典データセット
uspto-grants-2015_11
特許番号
US09175009B2

反応ノート

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