Diisopropylethylamine → tert-butyl (NE)-N-[[(9-bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carbonyl)amino]-methylsulfanylmethylidene]carbamate

HRID 886539노트

반응식

HRID 886539 반응식
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.[C:19]([NH:26][C:27]([S:29][CH3:30])=[NH:28])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]([N:28]=[C:27]([S:29][CH3:30])[NH:26][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582043519-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acidHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

생성물 1

HCID 178503947tert-butyl (NE)-N-[[(9-bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carbonyl)amino]-methylsulfanylmethylidene]carbamate수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

9-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid (3.2 g, 10.4 mmol), methyl N-Boc-carbamimidothioate (4.7 g, 12.4 mmol), HATU (5.0 g, 26.0 mmol) and DIPEA (6.7 g, 52.1 mmol) were dissolved in DCM (200 mL). After the resulting mixture was stirred at room temperature for 2 h, the reaction mixture was concentrated and methanol (50 mL) was added and filtered. The solid was collected to give methyl N′-9-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carbonyl-N-Boc-carbamimidothioate (3.0 g, 60%). 1H NMR (DMSO, 400 MHz) δ 12.84 (s, 1H), 8.31 (s, 1H), 8.18 (s, 1H), 7.32-7.27 (m, 2H), 5.72 (s, 1H), 4.49 (s, 4H), 2.30 (s, 3H), 1.49 (s, 9H)

후처리

  1. concentrationthe reaction mixture was concentrated
  2. additionmethanol (50 mL) was added
  3. filtrationfiltered
  4. customThe solid was collected

출처 및 근거

ORD 기록
ord-22c55835477c4321b69c530c15dfa0cf
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242104B2

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