HCID 135462952, compound → HCID 135830840, compound

HRID 1386016Notes

Reaction equation

HRID 1386016 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][C:3]=1[O:11][C:12]1[C:17]([F:18])=[C:16]([N:19]([CH3:30])[C:20]2([C:25]([O:27]CC)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:15]([F:31])=[C:14]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]3[N:40]([CH3:44])[CH2:41][CH2:42][N:43]=3)[CH:34]=2)[N:13]=1>Cl.C(#N)C.FC(F)(F)C(O)=O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][C:3]=1[O:11][C:12]1[C:17]([F:18])=[C:16]([N:19]([CH3:30])[C:20]2([C:25]([OH:27])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:15]([F:31])=[C:14]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]3[N:40]([CH3:44])[CH2:41][CH2:42][N:43]=3)[CH:34]=2)[N:13]=1

Participants

5

Reactant 1

HCID 135462952HCID 135462952, compound

Product 1

HCID 135830840HCID 135830840, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-hydroxy-3-[(4-(N-methyl-N-(1-ethoxycarbonylcyclopent-1-yl)amino)-6-(3-(1-methylimidazolin-2-yl)phenoxy)-3,5-difluoropyridin-2-yl)oxy]benzamidine, trifluoroacet acid salt (0.80 g, 1.2 mmol) in 25 mL of 6 N aqueous HCl was stirred at 60° C. for 1 hour. It was then cooled to ambient temperature, diluted with acetonitrile and trifluoroacetic acid and purified by HPLC on a C18 Dynamax column with 20-80% acetonitrile in water gradient with 0.1% trifluoroacetic acid to afford 4-hydroxy-3-[(4-(N-methyl-N-(1-carboxycyclopent-1-yl)amino)-6-(3-(1-methylimidazolin-2-yl)phenoxy)-3,5-difluoropyridin-2-yl)oxy]benzamidine, trifluoroacet acid salt as a white solid: NMR (DMSO-d6)/TFA) 10.2 (br s, 1), 9.0 (br s , 2), 8.8 (br s, 2), 7.3-7.6, (m, 6), 7.0 (d, 2), 4.1 (m, 2), 3.9 (m, 2), 3.2 (s, 3), 3.0 (s, 3), 2.9 (s, 3), 2.1 (m, 4), 1.6-1.8 n(m, 4) ppm.

Workup

  1. custompurified by HPLC on a C18 Dynamax column with 20-80% acetonitrile in water gradient with 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-e6e5a0ac8cc24dc38047ba5559a6e239
Source dataset
uspto-grants-2001_07
Patent number
US06265404B1

Reaction notes

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