1,2-Dichloroethane → HCID 67497138, compound

HRID 1628254Notes

Reaction equation

HRID 1628254 reaction equation
[NH2:1][C@@H:2]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:3]([NH:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH3:17])[CH:12]=2)=[N:8][C:7]=1[CH3:18])=[O:4].[S:27]1[CH:31]=[C:30]([CH:32]=O)[N:29]=[CH:28]1.C(Cl)Cl.CN(C)C=O.ClCCCl>>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@H:2]([NH:1][CH2:32][C:30]2[N:29]=[CH:28][S:27][CH:31]=2)[C:3]([NH:5][C:6]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([CH3:17])[CH:12]=3)=[N:8][C:7]=2[CH3:18])=[O:4])=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 2763214Thiazole-4-carboxaldehydeHCID 67496302HCID 67496302, compound

Product 1

HCID 67497138HCID 67497138, compoundYield 58.6%

Procedure

A mixture of (2S)-2-amino-3-(4-fluorophenyl)-N-(4-methyl-2-(2-methylpyridin-4-yl)thiazol-5-yl)propanamide (0.0500 g, 0.13 mmol), thiazole-4-carbaldehyde (0.015 g, 0.13 mmol), reactant 3 (0.10 g, 0.47 mmol), N,N-dimethylformamide (0.50 ml, 0.13 mmol) and 1,2-dichloroethane (1.50 ml, 0.13 mmol) was allowed to stir at rt overnight. The mixture was directly subjected to HPLC purification to give 35.6 mg of (2S)-3-(4-Fluorophenyl)-N-(4-methyl-2-(2-methylpyridin-4-yl)thiazol-5-yl)-2-(thiazol-4-ylmethylamino)propanamide 22. 400 MHz 1H NMR (CD3OD) δ: 9.12 (d, 1H), 8.64 (d, J=4.0 Hz, 1H), 8.28 (d, 1H), 8.22 (dd, J=8.0, 4.0 Hz, 1H), 7.82 (d, 1H), 7.26 (dd, 1H), 7.06 (dd, J=8.0, 8.0 Hz, 2H), 4.56 (dd, J=12.0, 8.0 Hz, 1H), 3.50 (dd, J=16.0, 8.0 Hz, 1H), 3.23 (dd, J=12.0, 8.0 Hz, 1H), 2.80 (s, 3H), 2.31 (s, 3H). LCMS (ES+) m/z 468.

Workup

  1. customThe mixture was directly subjected to HPLC purification

Sources & evidence

ORD record
ord-31a42075bc1546698c28de210966ddbd
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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