Aniline → HCID 86645560, compound

HRID 1879203Notes

Reaction equation

HRID 1879203 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:17]2[CH:21]=[CH:20][N:19]([CH2:22][CH2:23]OS(C)(=O)=O)[N:18]=2)[S:5][C:6]=1[C:7](=[O:16])[NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH2:36](Cl)Cl>C(OCC)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:7]([CH:6]2[S:5][C:4]([C:17]3[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:18]=3)=[N:3][C:2]2([CH3:36])[CH3:1])=[O:16])[CH:11]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 6344DichloromethaneHCID 59489547HCID 59489547, compound

Product 1

HCID 86645560HCID 86645560, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methanesulfonic acid 2-(3-{4-methyl-5-[(pyridin-3-ylmethyl)-carbamoyl]-thiazol-2-yl}-pyrazol-1-yl)-ethyl ester (0.19 g, 0.45 mmol) in methylene chloride (2 mL) was added aniline (0.91 mL, 9.93 mmol). The reaction mixture was heated under nitrogen at 85° C. for 16 hr. The reaction mixture was diluted with ethyl acetate (50 mL), washed with NaHCO3 (100 mL), water (100 mL) and brine (100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5) to provide 4-methyl-2-[1-(2-phenylamino-ethyl)-1H-pyrazol-3-yl]-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide as a white solid (0.052 g, 52%). 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.58 (d, J=4 Hz, 1H), 7.78 (d, J=8 Hz, 1H), 7.41 (d, J=2 Hz, 1H), 7.32-7.37 (m, 1H), 7.17-7.23 (m, 2H), 6.83 (d, J=2 Hz, 1H), 6.76 (t, J=8 Hz, 1H), 6.63 (d, J=5 Hz, 2H), 6.18-6.23 (m, 1H), 4.67 (d, J=8 Hz, 2H), 4.38 (t, J=4 Hz, 2H), 3.68 (t, J=4 Hz, 2H), 2.77 (s, 3H); MS (M+H)+=419.2; Rt=1.23 min; HRMS (M+H)+=419.17.

Workup

  1. washwashed with NaHCO3 (100 mL), water (100 mL) and brine (100 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-12f161fa54114acb9792a69d81d5e388
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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