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

HRID 563430Notes

Reaction equation

HRID 563430 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:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:11]([C:15]3[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=3)[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 249377433-(1H-indazol-5-yl)-2,3-diphenyl-N-(1,3,4-thiadiazol-2-yl)propanamide

Procedure

Example 152 was prepared from 3-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoic acid (10 and 30 mg, 0.03 and 0.88 mmol) and 1,3,4-thiadiazol-2-amine using General Coupling Method A to give 4 mg (% yield) and 6 mg of the respective diastereomers. MS found: (M+H)+=426. NMR(CDCl3) δ 8.8 (s, 1H); 7.97-8.01 (d, 1H); 7.60 (s, 1H) 7.0-7.59 (m, 12H); 4.85 (d, 1H); 4.56 (d, 1H).

Workup

  1. customto give 4 mg (% yield) and 6 mg of the respective diastereomers

Sources & evidence

ORD record
ord-e30fd42e78e541ab9c1e223d1b733928
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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