1,2-Dichloroethane → HCID 67497281, compound

HRID 1628211Notes

Reaction equation

HRID 1628211 reaction equation
[NH2:1][C@@H:2]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[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:24]1[CH:28]=[C:27]([CH:29]=O)[N:26]=[CH:25]1.CN(C)C=O.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:18]1([CH2:17][C@H:2]([NH:1][CH2:29][C:27]2[N:26]=[CH:25][S:24][CH:28]=2)[C:3]([NH:5][C:6]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:8][CH:7]=2)=[O:4])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 2763214Thiazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67496787HCID 67496787, compound

Product 1

HCID 67497281HCID 67497281, compoundYield 10.3%

Procedure

To a mixture of (S)-2-amino-3-phenyl-N-(2-(pyridin-4-yl)thiazol-5-yl)propanamide (0.075 g, 0.23 mmol), thiazole-4-carbaldehyde (0.026 g, 0.23 mmol) and N,N-dimethylformamide (0.500 ml, 0.23 mmol) in 1,2-dichloroethane (1.000 ml, 0.23 mmol) was added sodium triacetoxyborohydride (0.17 g, 0.81 mmol). The resulting mixture was allowed to stir at room temperature for 4 hours. Upon completion, the mixture was directly subjected to HPLC purification give 10 mg of (S)-3-phenyl-N-(2-(pyridin-4-yl)thiazol-5-yl)-2-(thiazol-4-ylmethylamino)-propanamide 5.3. 400 MHz 1H NMR (CD3OD) δ: 9.30 (d, 1H), 8.81 (d, 2H), 8.07 (d, 2H), 7.95 (d, 1H), 7.76 (s, 1H), 7.28-7.37 (m, 3H), 7.24 (dd, J=8.0, 4.0 Hz, 2H), 4.49 (d, J=16 Hz, 1H), 4.44 (d, J=16 Hz, 1H), 4.43 (dd, J=12, 8.0 Hz, 1H), 3.49 (dd, J=12, 4.0 Hz, 1H), 3.23 (dd, J=12, 8.0 Hz, 1H). LCMS (ES+) m/z 422.

Workup

  1. customUpon completion, the mixture was directly subjected to HPLC purification

Sources & evidence

ORD record
ord-d5906f1fc6fb4fa58aa2e7753283fee3
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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