1,2-Dichloroethane → HCID 67497900, compound

HRID 1628207Notes

Reaction equation

HRID 1628207 reaction equation
[NH2:1][C@@H:2]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:3]([NH:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:8][CH:7]=1)=[O:4].[S:25]1[CH:29]=[C:28]([CH:30]=O)[N:27]=[CH:26]1.CN(C)C=O.ClCCCl.C(Cl)Cl>>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C@H:2]([NH:1][CH2:30][C:28]2[N:27]=[CH:26][S:25][CH:29]=2)[C:3]([NH:5][C:6]2[S:10][C:9]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)=[N:8][CH:7]=2)=[O:4])=[CH:23][CH:22]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 2763214Thiazole-4-carboxaldehydeHCID 67496839HCID 67496839, compound

Product 1

HCID 67497900HCID 67497900, compoundYield 63.7%

Procedure

To a mixture of (S)-2-amino-3-(4-fluorophenyl)-N-(2-(pyridin-4-yl)thiazol-5-yl)propanamide (0.090 g, 0.20 mmol), thiazole-4-carbaldehyde (0.022 g, 0.20 mmol), N,N-dimethylformamide (0.014 g, 0.20 mmol) and 1,2-dichloroethane (0.020 g, 0.20 mmol) was added Reactant 3 (0.19 g, 0.89 mmol). The resulting mixture was allowed to stir at rt overnight. The mixture was directly purified HPLC to give 56 mg of (S)-3-(4-Fluorophenyl)-N-(2-(pyridin-4-yl)thiazol-5-yl)-2-(thiazol-4-ylmethylamino)propanamide 5.2. 400 MHz 1H NMR (CD3OD) δ: 9.09 (d, J=4.0 Hz, 1H), 8.78 (d, 2H), 8.34 (d, J=8.0 Hz, 2H), 7.80 (d, 1H), 7.74 (s, 1H), 7.24 (dd, J=8.0, 4.0 Hz, 2H), 7.04 (, J=12, 8.0 hz, 2H), 4.54 (d, J=16 Hz, 1H), 4.50 (d, J=16 Hz, 1H), 4.40 (dd, J=12.0, 8.0 Hz, 1H), 3.47 (dd, J=16.0, 8.0 Hz, 1H), 3.26 (dd, J=16.0, 8.0 Hz, 1H). LCMS (ES+) m/z 440.

Sources & evidence

ORD record
ord-db4b5ac40ad246c4b80aa5ff6a386fe1
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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