Ethanol → HCID 22614920, compound

HRID 843120Notes

Reaction equation

C1(N[C:5]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]4[O:19][C:20]5[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH2:32][CH2:33][NH:34][CH2:35][C:36]6[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=6)[C:21]=5[C:22]=4C4CC4)=[CH:12][C:10]=3[CH:11]=2)=O)CC1.[CH3:42][CH2:43][OH:44].[CH3:45]N(C)C=O.CN1CC[CH2:53][C:52]1=O>>[CH2:43]([O:44][CH2:5][C:7]1[O:8][C:9]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[O:19][C:20]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH:31]5[CH2:32][CH2:33][N:34]([CH2:35][C:36]6[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=6)[CH2:53][CH2:52]5)[C:21]=4[C:22]=3[CH3:45])=[CH:12][C:10]=2[CH:11]=1)[CH3:42]

Participants

Reactant 4

HCID 702Ethanol

HCID 6228Dimethylformamide

HCID 13387N-methyl-2-pyrrolidone

HCID 68658399HCID 68658399, compound

Product 1

HCID 22614920HCID 22614920, compound

Procedure

Phenol 45 is reacted with Br—Q1—Br in a solvent such as acetone, 2-butanone, acetonitrile and N,N-dimethylformamide (DMF) in the presence of a base such as sodium hydride, potassium carbonate and cesium carbonate at a temperature between −20° C. and 100° C., preferably at 20° C. to 85° C. to give bromide 48. Bromide 48 can be reacted with amine, NH(Q2R6)(Q3R7), in the absence or in the presence of a solvent such as EtOH, DMF and N-methyl-2-pyrrolidone at a temperature between 0° C. and 150° C., preferably at 20° C. to 130° C., to give an amino derivative 49.

Sources & evidence

ORD record: ord-e86146b789b849b4932250fb4e8b21e4
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376491B1

Reaction notes

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