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

HRID 1692214Notes

Reaction equation

HRID 1692214 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-13e4f9e460db41ed8d5da14d78612f0b
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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