Triethylamine → HCID 86592547, compound

HRID 1432986Notes

Reaction equation

HRID 1432986 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][C@@H:17]([CH3:19])[NH:16][C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:29][C:30]1[S:34][C:33]([CH:35]=[CH:36][S:37](Cl)(=[O:39])=[O:38])=[CH:32][CH:31]=1>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][C@@H:17]([CH3:19])[N:16]([S:37]([CH:36]=[CH:35][C:33]4[S:34][C:30]([Cl:29])=[CH:31][CH:32]=4)(=[O:39])=[O:38])[C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chlorideHCID 57308893HCID 57308893, compound

Product 1

HCID 86592547HCID 86592547, compoundYield 2.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,5R)-1-(4-Amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one (43 mg, 0.123 mmol), minor epimer from EXAMPLE 88, Part D, is taken up in methylene chloride to this is added triethylamine (0.034 ml, 0.25 mmol) followed by 2-(5-chloro-thiophen-2-yl)-ethenesulfonyl chloride (40 mg, 0.16 mmol), EXAMPLE 3. The reaction is stirred overnight, and the crude material is purified by preparative thin layer chromatography (15% methanol/CH2Cl2). The product (1.4 mg, 2.3%) is isolated as a yellow wax. C21H22ClN5O3S2 MS m/z: 492, 494. 1H NMR (CD3OD) δ8.36 (s, 1H); 8.03 (d, 1H, J=7.5 Hz); 7.61 (s, 1H); 7.49-7.44 (m, 2H); 7.19 (d, 1H, J=3.83 Hz); 6.98 (d, 1H, J=3.75 Hz); 6.76 (d, 1H, J=15.1 Hz); 4.86-4.71 (m, 2H); 4.45-4.39 (m, 1H); 4.13-4.09 (m, 1H); 3.64-3.7 (m, 2H); 1.63 (d, 3H, J=7.09 Hz); 1.33 (d, 3H, J=6.80 Hz).

Workup

  1. customthe crude material is purified by preparative thin layer chromatography (15% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-f77550b7903c4bbeb5e47dd7d8f30d14
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…