4-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoic Acid → HCID 18422086, compound

HRID 1281727Notes

Reaction equation

HRID 1281727 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[N:6]=1.[NH2:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:30]=2)=[O:28])[CH:22]=[CH:23][C:24]=1[CH3:25]>>[CH3:25][C:24]1[CH:23]=[CH:22][C:21]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[CH:30]=2)=[O:28])=[CH:20][C:19]=1[NH:18][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 49628404-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoic AcidHCID 17904941N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide

Product 1

HCID 18422086HCID 18422086, compound

Procedure

Using an analogous procedure to that described in the first paragraph of Example 26, 4-(2-methylthiazol4-ylmethoxy)benzoic acid was reacted with N-(3-amino4-methylphenyl)-2-morpholinopyridine-4-carboxamide. The reaction product was purified by column chromatography on silica using a 97:3 mixture of methylene chloride and methanol as eluent. There was thus obtained to give the title compound; NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 2.44 (s, 3H), 3.5 (t, 4H), 3.7 (t, 4H), 5.19 (s, 2H), 7.11 (m, 3H), 7.23 (m, 2H), 7.4 (t, 2H), 7.54 (m, 3H), 7.68 (d, 1H), 7.78 (d, 1H), 7.96 (d, 2H), 8.24 (d, 1H), 9.73 (s, 1H), 10.27 (s, 1H); Mass Spectrum: M+H+ 544.

Workup

  1. customThe reaction product was purified by column chromatography on silica using
  2. additiona 97:3 mixture of methylene chloride and methanol as eluent
  3. customThere was thus obtained

Sources & evidence

ORD record
ord-49c9418ccc4941f5a9a44396021ce9ae
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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