Diisopropylethylamine → 2-Ethyl-N-(1-methyl-1H-pyrazol-3-yl)-4-[4-(methylsulfonyl)-phenoxy]-1-benzofuran-6-carboxamide

HRID 1177265Notes

Reaction equation

HRID 1177265 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12](O)=[O:13])[CH:9]=[C:8]([O:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[C:6]=2[CH:7]=1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:59][N:60]1[CH:64]=[CH:63][C:62]([NH2:65])=[N:61]1>CN(C=O)C.O>[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([NH:65][C:62]3[CH:63]=[CH:64][N:60]([CH3:59])[N:61]=3)=[O:13])[CH:9]=[C:8]([O:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][CH:17]=3)[C:6]=2[CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595599412-Ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylic acid

Product 1

HCID 595601602-Ethyl-N-(1-methyl-1H-pyrazol-3-yl)-4-[4-(methylsulfonyl)-phenoxy]-1-benzofuran-6-carboxamideYield 22.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylic acid (400 mg, 1.1 mmol), HATU (635 mg, 1.6 mmol) and DIPEA (214 mg, 1.6 mmol) in DMF (20 mL) was stirred for 1 h. Then, 1-methyl-1H-pyrazol-3-amine (129 mg, 1.3 mmol) was added. The resulting solution was stirred overnight. The reaction was monitored by TLC (petroleum ether/EtOAc 1:1). The mixture was poured into water (30 mL) and extracted with EtOAc (30 mL×3). The organic layer was washed with brine (20 mL×2), dried over Na2SO4, concentrated and purified by preparative HPLC to afford the desired product (109.5 mg, 22%) as a yellow solid. 1H NMR (400 MHz, DMSO): δ 10.89 (s, 1H), 8.15 (s, 1H), 7.94 (d, 2H), 7.65 (s, 1H), 7.00 (s, 1H), 7.24 (d, 2H), 6.61 (s, 1H), 6.55 (d, 2H), 3.77 (s, 3H), 3.20 (s, 3H), 2.82 (q, 2H), 1.25 (t, 3H); MS (APCI, pos): 440.3.

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. washThe organic layer was washed with brine (20 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7babcc0dbf4945b4acc636b07305b172
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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