1,3,4-Thiadiazol-2-amine → 3-(1H-indazol-5-yl)-2-methyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide

HRID 563426Notes

Reaction equation

HRID 563426 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]([CH3:15])[C:12]([OH:14])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[S:22]1[CH:26]=[N:25][N:24]=[C:23]1[NH2:27]>>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]([CH3:15])[C:12]([NH:27][C:23]3[S:22][CH:26]=[N:25][N:24]=3)=[O:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 670058283-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoic acid

Product 1

HCID 249377423-(1H-indazol-5-yl)-2-methyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamideYield 42%

Procedure

Example 151 was prepared from 3-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoic acid (40 mg, 0.26 mmol) and 1,3,4-thiadiazol-2-amine using General Coupling Method A to give 6 mg (42% yield). MS found: (M+H)+=364. 400 MHz 1H-NMR (CDCl3) δ 8.77 (s, 1H); 7.90 (s, 1H); 7.75 (s, 1H); 7.75 (s, 1H); 7.47 (m, 4H); 7.36 (app t, 2H); 7.25 (dd, 2H); 4.35 (d, 1H); 3.87 (m, 1H); 1.31 (d, 3H).

Workup

  1. customto give 6 mg (42% yield)

Sources & evidence

ORD record
ord-fa0dd1b1d3d842faaa9f97b50e28b08e
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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