4-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoic Acid → N-{4-methyl-3-[4-(2-methylthiazol-4-ylmethoxy)benzamido]phenyl}dibenzofuran-4-carboxamide

HRID 1281730Notes

Reaction equation

HRID 1281730 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[C:34]3[O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:33]=3[CH:32]=[CH:31][CH:30]=2)=[O:28])[CH:22]=[CH:23][C:24]=1[CH3:25]>C(Cl)Cl>[CH3:25][C:24]1[CH:23]=[CH:22][C:21]([NH:26][C:27]([C:29]2[C:34]3[O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:33]=3[CH:32]=[CH:31][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

4

Reactant 2

HCID 49628404-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoic AcidHCID 22594118HCID 22594118, compound

Product 1

HCID 18422115N-{4-methyl-3-[4-(2-methylthiazol-4-ylmethoxy)benzamido]phenyl}dibenzofuran-4-carboxamideYield 24.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Methylthiazol-4-ylmethoxy)benzoic acid (0.095 g) was added to a stirred mixture of N-(3-amino-4-methylphenyl)dibenzofuran-4-carboxamide (0.12 g), diisopropyethyllamine (0.2 ml), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.134 g) and methylene chloride (22 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was purified by column chromatography on an ion exchange column (isolute SCX column) using initially a 1:1 mixture of ethyl acetate and methanol and then a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. The product so obtained was triturated under ethyl acetate. There was thus obtained the title compound (0.051 g); NMR Spectrum: (DMSOd6) 2.25 (s, 3H), 2.65 (s, 3H), 5.2 (s, 2H), 7.15 (d, 2H), 7.25 (d, 1H),7.4-7.65 (m, 5H), 7.8-7.9 (m, 3H), 7.98 (d, 2H), 8.2 (d, 1H), 8.35 (d, 1H), 9.8 (d, 1H), 10.4 (s, 1H); Mass Spectrum: M+H+ 548.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on an ion exchange column (isolute SCX column)
  3. additiona 1:1 mixture of ethyl acetate and methanol
  4. additiona 99:1 mixture of methanol
  5. customThe product so obtained
  6. customwas triturated under ethyl acetate

Sources & evidence

ORD record
ord-38daf654bff441a3a828ad9c875b41fa
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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