Benzoic Acid → HCID 86620398, compound

HRID 252723Notes

Reaction equation

HRID 252723 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[NH2:19][C:20]1[S:21][C:22]([C:26]2[CH:27]=[C:28]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:29]([Cl:32])=[N:30][CH:31]=2)=[C:23]([CH3:25])[N:24]=1>CC(N(C)C)=O>[Cl:32][C:29]1[N:30]=[CH:31][C:26]([C:22]2[S:21][C:20]([NH:19][C:1](=[O:9])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:24][C:23]=2[CH3:25])=[CH:27][C:28]=1[NH:33][S:34]([CH3:37])(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 86620384HCID 86620384, compound

Product 1

HCID 86620398HCID 86620398, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of benzoic acid (27 mg), diisopropylethylamine (0.053 mL), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (84 mg) and DMA (0.5 mL) was stirred at room temperature under an atmosphere of nitrogen for 5 minutes. N-[5-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]methanesulfonamide (32 mg) was added and the mixture was stirred and heated to 80° C. for 30 minutes. The solvent was evaporated and the residue was triturated under water. The resultant gum was purified by HPLC using a Phenomenex ‘Luna’ preparative reversed-phase column (10 microns silica, 21 mm diameter, 150 mm length) using decreasingly polar mixtures of water (containing 0.2% trifluoroactic acid) and acetonitrile as eluent. There was thus obtained the title compound as a solid (17 mg); NMR Spectrum: (DMSOd6) 2.44 (s, 3H), 3.19 (s, 3H), 7.57 (t, 2H), 7.64-7.69 (m, 1H), 7.95 (s, 1H), 8.12 (d, 2H), 8.42 (s, 1H), 9.91 (s, 1H), 12.87 (s, 1H): Mass Spectrum: M−H− 421.

Workup

  1. stirringthe mixture was stirred
  2. temperatureheated to 80° C. for 30 minutes
  3. customThe solvent was evaporated
  4. customthe residue was triturated under water
  5. customThe resultant gum was purified by HPLC

Sources & evidence

ORD record
ord-e017d1f950d040b9b0ba1fff3550d0ee
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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