4-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid → 4-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid

HRID 2190600Notes

Reaction equation

HRID 2190600 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23](=[O:33])[NH:24][C:25]4[CH:30]=[C:29]([I:31])[CH:28]=[C:27]([F:32])[CH:26]=4)=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.C(C1C=C(NC(C2C=CC(N3CCN(C4C=CC(C(O)=O)=CC=4)CC3)=NC=2)=O)C=CC=1)(C)(C)C>>[F:32][C:27]1[CH:26]=[C:25]([NH:24][C:23]([C:20]2[CH:21]=[CH:22][C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:34])=[O:3])=[CH:6][CH:7]=4)[CH2:16][CH2:15]3)=[N:18][CH:19]=2)=[O:33])[CH:30]=[C:29]([I:31])[CH:28]=1

Participants

3

Reactant 2

HCID 462019764-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acidHCID 593181614-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester

Product 1

HCID 593180834-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid

Procedure

4-{4-[5-(3-Fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid was prepared by the hydrolysis of 4-{4-[5-(3-fluoro-5-iodo-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid ethyl ester with LiOH monohydrate in manner similar to the one described in the synthesis of 4-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid, above. The product was obtained after suspension in small volume of EtOAc, filtration and a wash with CH3CN. HRMS m/z calcd for C23H20N4O3FI [M+H]+: 547.0637. Found: 547.0634.

Workup

  1. customThe product was obtained after suspension
  2. filtrationin small volume of EtOAc, filtration
  3. washa wash with CH3CN

Sources & evidence

ORD record
ord-0a7fb9e6eb3d4f52aea23ab96d6cb23e
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

Loading…