N-bromobutanimide → N-(2-ethoxy-5,6-difluorophenethyl)-N'-(5-bromopyrid-2-yl)-urea

HRID 842643Notes

Reaction equation

C([O:3]C1C=CC(F)=C(F)C=1CCN)C.[CH2:15]([O:17][C:18]1[CH:36]=[CH:35][C:34]([F:37])=[C:33]([F:38])[C:19]=1[CH2:20][CH2:21][NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1)=S)[CH3:16].C1C(=O)N(Br)C(=O)C1>>[CH2:15]([O:17][C:18]1[CH:36]=[CH:35][C:34]([F:37])=[C:33]([F:38])[C:19]=1[CH2:20][CH2:21][NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1)=[O:3])[CH3:16]

Participants

Reactant 3

HCID 67184N-bromobutanimide

HCID 3001126Thiourea, N-(5-bromo-2-pyridinyl)-N'-(2-(6-ethoxy-2,3-difluorophenyl)ethyl)-

HCID 107981222-Ethoxy-5,6-difluoro-phenethylamine

Product 1

HCID 22615117N-(2-ethoxy-5,6-difluorophenethyl)-N'-(5-bromopyrid-2-yl)-urea

Procedure

The methods described in Example 151 of WO 93/03022 was then used to transform this compound to 2-ethoxy-5,6-difluoro-phenethylamine. The method described in Example 411 of WO 93/03022 was then used to prepare N-(2-ethoxy-5,6-difluorophenethyl)-N′-(5-bromopyrid-2-yl)-thiourea. This product was then oxidised with NBS as Example 4 to provide N-(2-ethoxy-5,6-difluorophenethyl)-N′-(5-bromopyrid-2-yl)-urea. 1H-NMR (250 MHz, CDCl3): 1.4 (t, 3H), 3.0 (q, 2H), 3.95 (q, 2H), 6.5 (m, 1H), 6.8 (d, 1H), 6.95 (dd, 1H), 7.68 (dd, 1H), 8.90 (d, 1H) 8.9 (s, 1H), 9.0 (s, 1H).

Sources & evidence

ORD record: ord-23d11c754bf642af96c37416ace8c83a
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376492B1

Reaction notes

Loading…