{2-[3-Chloro-5-(3-fluorophenyl-(3-tetrazol-2-yl-propyl)-carbamoyl)-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester → 3-Chloro-N-(3-fluoro-phenyl)-5-[2-(pyridin-4-ylamino)-ethoxy]-N-(3-tetrazol-2-yl-propyl)-benzamide

HRID 2268677Notes

Reaction equation

HRID 2268677 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](=[O:40])[N:24]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[CH2:25][CH2:26][CH2:27][N:28]2[N:32]=[N:31][CH:30]=[N:29]2)[CH:20]=[C:19]([Cl:41])[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[Cl:41][C:19]1[CH:20]=[C:21]([CH:22]=[C:17]([O:16][CH2:15][CH2:14][NH:7][C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH:18]=1)[C:23]([N:24]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1)[CH2:25][CH2:26][CH2:27][N:28]1[N:32]=[N:31][CH:30]=[N:29]1)=[O:40]

Participants

4

Reactant 1

HCID 54468377{2-[3-Chloro-5-(3-fluorophenyl-(3-tetrazol-2-yl-propyl)-carbamoyl)-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 183491323-Chloro-N-(3-fluoro-phenyl)-5-[2-(pyridin-4-ylamino)-ethoxy]-N-(3-tetrazol-2-yl-propyl)-benzamideYield 72.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {2-[3-chloro-5-(3-fluorophenyl-(3-tetrazol-2-yl-propyl)-carbamoyl)-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester (0.07 g) in trifluoroacetic acid (0.75 ml) and dichloromethane (0.75 ml) was stirred at room temperature for 1 h then concentrated under vacuum. The residue was purified by flash chromatography, eluting with dichloromethane/methanol/ammonia (90:10:1) to give the title compound as a white foam (0.042 g).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was purified by flash chromatography
  3. washeluting with dichloromethane/methanol/ammonia (90:10:1)

Sources & evidence

ORD record
ord-751d1bdf21b94541aa3f8fc708d7ac2e
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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