Dimethyl Sulfoxide → 1-[(3-Chloroquinoxalin-2-yl)amino]-4-phenylbutan-2-one

HRID 389076Notes

Reaction equation

HRID 389076 reaction equation
[Cl:1][C:2]1[C:3]([NH:12][CH2:13][CH:14]([OH:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.ClC1C(NCC(=O)CC(C)C)=NC2C(N=1)=CC=CC=2.CS(C)=O.N(C)(C)C>CCN(CC)CC>[Cl:1][C:2]1[C:3]([NH:12][CH2:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1146TrimethylamineHCID 859636811-[(3-Chloroquinoxalin-2-yl)amino]-4-methylpentan-2-oneHCID 866458901-[(3-Chloroquinoxalin-2-yl)amino]-4-phenylbutan-2-ol2×

Product 1

HCID 859636851-[(3-Chloroquinoxalin-2-yl)amino]-4-phenylbutan-2-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3b is prepared from 2b according to the protocol described for 3a; 2b (4.7 g, 14.4 mmol), 14.4 ml DMSO, 14.4 ml Et3N, and Me3N.SO3 (4 g, 28.8 mmol). The product is purified by chromatography on a silica column, eluent: C6H12/Et2O (80:20) to give a yellow solid (4.51 g, 96%); 1H NMR (100 MHz, CDCl3) δ: 2.82-3.01 (m, 4H), 4.38 (d, J=5 Hz, 2H), 6.4 (m, 1H), 7.23-7.84 (m, 9H). Analysis calculated for C18H16N3OCl: C, 66.36; H, 4.95; N, 12.90. Experimental: C, 66.53; H, 5.23; N, 12.78.

Workup

  1. customThe product is purified by chromatography on a silica column, eluent

Sources & evidence

ORD record
ord-3ee4c65a9f2d40b59e826694083bf41e
Source dataset
uspto-grants-2013_02
Patent number
US08378098B2

Reaction notes

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