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

HRID 1800364Notes

Reaction equation

HRID 1800364 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)

Workup

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

Sources & evidence

ORD record
ord-618506279b8442bd8d7934e84cd552ef
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

Loading…