o-Phenetidine → HCID 86706296, compound

HRID 2205883Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:18]3[CH:19]=[N:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:22]=3)[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]=2[CH:3]=1.[CH2:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH2:39])[CH3:31]>>[C:26]([O:25][C:23]([N:21]1[CH:22]=[C:18]([C:9]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]3[CH:3]=[C:2]([NH:39][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[O:32][CH2:30][CH3:31])[N:7]=[CH:6][C:5]=3[CH:8]=2)[CH:19]=[N:20]1)=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

Reactant 2

HCID 7203o-Phenetidine

HCID 86706270HCID 86706270, compound

Product 1

HCID 86706296HCID 86706296, compoundYield 33%

Procedure

The title compound was prepared in 33% yield from compound (10) and 2-ethoxyphenylamine using the method described for Preparation 35. 1H-NMR (CDCl3, 500 MHz): δ 1.48 (t, J=6.94 Hz, 3H), 1.54 (s, 9H), 1.69 (s, 9H), 4.14 (q, J=6.94 Hz, 2H), 6.59 (d, J=0.63 Hz, 1H), 6.91-6.98 (m, 3H), 7.11 (br s, 1H), 7.70 (m, 1H), 7.83 (d, J=0.63 Hz, 1H), 7.91 (br d, J=8.20 Hz, 1H), 8.33 (d, J=0.63 Hz, 1H), 8.49 (s, 1H).

Workup

customdescribed for Preparation 35

Sources & evidence

ORD record: ord-a685a24bb17c47278b6a1720103bfb3f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371319B2

Reaction notes

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