Ethyl bromoacetate → HCID 10528902, compound

HRID 2228554Notes

Reaction equation

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

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 11795219HCID 11795219, compound

Product 1

HCID 10528902HCID 10528902, compound

Procedure

Using a procedure similar to Example 2A except starting with N1-(3-cyanobenzoyl)-N2-(4-isopropylbenzoyl)-4-hydroxy-1,2-benzenediamine and ethyl bromoacetate, the title compound was obtained as a solid (78%); IR(CHCl3): 2966, 1757, 1655, 1610, 1514 cm−1; NMR(300 MHz, CDCl3): δ1.31 (m, 9H), 3.00 (m, 1H), 4.24 (t, 2H, J=6.9 Hz), 4.35 (s, 2H), 6.59 (d, 1H, J=9.0 Hz), 6.95 (s, 1H), 7.35 (m, 3H), 7.64 (m, 1H), 7.82 (d, 1H, J=7.5 Hz), 7.92 (d, 2H, J=8.1 Hz), 8.23 (d, 1H, J=7.5 Hz), 8.32 (s, 1H), 9.06 (br s, 1H), 9.61 (br s, 1H); MS(FD): 485.2.

Sources & evidence

ORD record: ord-19cc25bb013641a193c1ded36ac1d5c5
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417200B1

Reaction notes

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