Diisopropylethylamine → HCID 59489531, compound

HRID 1879227Notes

Reaction equation

HRID 1879227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]3[S:17][C:18]([C:22]([OH:24])=[O:23])=[C:19]([CH3:21])[N:20]=3)=[N:11]2)=[CH:4][CH:3]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]CN)[CH:26]=1.F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]3[S:17][C:18]([C:22]([OH:24])=[O:23])=[C:19]([CH3:21])[N:20]=3)=[N:11]2)=[CH:4][CH:3]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][NH:41][C:22]([C:18]2[S:17][C:16]([C:12]3[CH:13]=[C:14]([CH3:15])[N:10]([CH2:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:11]=3)=[N:20][C:19]=2[CH3:21])=[O:24])[CH:26]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 68492548HCID 68492548, compound

Product 2

HCID 59489531HCID 59489531, compoundYield 55.5%HCID 68492548HCID 68492548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-{1-[2-(4-fluoro-phenyl)-ethyl]-5-methyl-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (0.15 g, 0.43 mmol) in methylene chloride (10 mL) was added 2-pyridin-3-yl-ethylamine (0.05 g, 0.48 mmol), benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.21 g, 0.48 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.87 mmol). The reaction 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 (methylene chloride:methanol, 98:2) to provide 2-{1-[2-(4-fluoro-phenyl)-ethyl]-5-methyl-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl-amide as a white solid (0.052 g, 29% yield). 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.57 (d, J=4 Hz, 1H), 7.73 (d, J=4 Hz, 1H), 7.27-7.32 (m, 1H), 6.90-6.99 (m, 4H), 6.49 (s, 1H), 6.05-6.11 (bm, 1H), 4.64 (d, J=4 Hz, 2H), 4.23 (t, J=7 Hz, 2H), 3.13 (t, J=7 Hz, 2H), 2.76 (s, 3H), 1.56 (s, 3H); MS (M+H)+=435.9; Rt=1.31 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 (methylene chloride:methanol, 98:2)

Sources & evidence

ORD record
ord-aac8dc3532a045bc8355f32f997ed3ab
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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