1,3,4-Thiadiazol-2-amine → 3-(1-(4-Fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethyl-N-(1,3,4-thiadiazol-2-yl)hexanamide

HRID 563366Notes

Reaction equation

HRID 563366 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18]([CH3:23])([CH3:22])[C:19](O)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[S:28]1[CH:32]=[N:31][N:30]=[C:29]1[NH2:33]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([CH2:24][CH:25]([CH3:26])[CH3:27])[C:18]([CH3:23])([CH3:22])[C:19]([NH:33][C:29]4[S:28][CH:32]=[N:31][N:30]=4)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 670054443-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoic acid

Product 1

HCID 592528213-(1-(4-Fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethyl-N-(1,3,4-thiadiazol-2-yl)hexanamideYield 24%

Procedure

To a solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhexanoic acid (220 mg, 0.6 mmol) from Example 33(c) was coupled to 1,3,4-thiadiazol-2-amine (60 mg, 0.6 mmol) using General Coupling Method B. The product was purified by HPLC to give 33 mg (24%) of the desired product Example 34. MS found: (M+H)+=452. NMR(CDCl3) δ 8.73 (s, 1H); 8.11 (s, 1H); 7.8-8.4 (bs, 1H) 7.55-7.61 (m, 3H); 7.49-7.51 (d, 1H); 7.28-7.30 (d, 1H); 7.14-7.19 (m, 3H); 3.31-3.36 (dd, 1H), 1.88-1.95 (dt, 1H); 1.26 (s, 3H); 1.15 (s, 3H); 0.6-0.8 (dd, 6H).

Workup

  1. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-2fd8c3260ffa4d82bed1ac6e5bc14964
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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