Methanol → 4-[2-(5-amino-1H-pyrazol-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1401918Notes

Reaction equation

HRID 1401918 reaction equation
C([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[OH:17])[C:7]([NH:18]C(=O)C(F)(F)F)=[N:6]1)(C)(C)C.[Cl:25][C:26]1[C:27](F)=[CH:28][C:29]([F:52])=[C:30]([S:32]([N:35](CC2C=CC(OC)=CC=2OC)[C:36]2[S:37][CH:38]=[N:39][N:40]=2)(=[O:34])=[O:33])[CH:31]=1.CO>Cl>[NH2:18][C:7]1[NH:6][N:5]=[CH:9][C:8]=1[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][C:27]1[C:26]([Cl:25])=[CH:31][C:30]([S:32]([NH:35][C:36]2[S:37][CH:38]=[N:39][N:40]=2)(=[O:33])=[O:34])=[C:29]([F:52])[CH:28]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 86643821N-(1-(tert-butyl)-4-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-3-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 468412174-[2-(5-amino-1H-pyrazol-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The title compound was prepared from N-[1-tert-Butyl-4-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-3-yl]-2,2,2-trifluoroacetamide (Preparation 209) and 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 247) using Method B above with the exception that heating at 55° C. in HCl (gas) saturated methanol for 16 hours was used to remove the protecting groups. Purification by preparative HPLC afforded the title compound.

Workup

  1. customto remove the protecting groups
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-b05ae0c1a577481eab99dd9c2c54e563
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

Loading…