Diisopropylethylamine → HCID 24951861, compound

HRID 1879218Notes

Reaction equation

HRID 1879218 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[N:19]=3)=[N:11]2)=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][NH2:32])[CH:25]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][NH:32][C:21]([C:17]2[S:16][C:15]([C:12]3[CH:13]=[CH:14][N:10]([CH2:9][CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[N:11]=3)=[N:19][C:18]=2[CH3:20])=[O:23])[CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 68490567HCID 68490567, compound

Product 1

HCID 24951861HCID 24951861, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-{1-[2-(4-fluoro-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (0.1 g, 0.30 mmol) in methylene chloride (5 mL) was added 2-pyridin-3-yl-ethylamine (0.04 g, 0.33 mmol), benzotriazol-1-yloxytris(dimethylamino)-hexafluorophosphate (0.146 g, 0.33 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.60 mmol) and the mixture was stirred under nitrogen at room temperature for 16 hr. The reaction mixture was diluted with methylene chloride (50 mL), washed with water (50 mL) and brine (2×50 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel eluting with 50% ethyl acetate, 50% hexane to provide 2-{1-[2-(4-fluoro-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (2-pyridin-3-yl-ethyl)-amide as a white solid (0.095 g, 73%). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=2 Hz, 2H), 7.58 (d, J=4 Hz, 1H), 7.25-7.28 (m, 1H), 7.14 (d, J=2 Hz, 1H), 6.90-7.03 (m, 4H), 6.70 (d, J=2 Hz, 1H), 5.96-6.03 (m, 1H), 4.34 (t, J=7 Hz, 2H), 3.65-3.73 (m, 2H), 3.17 (t, J=7 Hz, 2H), 2.95 (t, J=7 Hz, 2H), 2.68 (s, 3H). MS (M+H)+=436.2; Rt=1.28 min; HRMS (M+H)+=436.16.

Workup

  1. washwashed with water (50 mL) and brine (2×50 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 eluting with 50% ethyl acetate, 50% hexane

Sources & evidence

ORD record
ord-5682c30a402848a993dded9f2243ebe2
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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