Triethylamine → Taprenepag isopropyl

HRID 1437123Notes

Reaction equation

HRID 1437123 reaction equation
[N:1]1([C:6]2[CH:28]=[CH:27][C:9]([CH2:10][NH:11][CH2:12][C:13]3[CH:14]=[C:15]([CH:24]=[CH:25][CH:26]=3)[O:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C(N(CC)CC)C.[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([S:42](Cl)(=[O:44])=[O:43])[CH:37]=1>ClCCl>[N:1]1([C:6]2[CH:28]=[CH:27][C:9]([CH2:10][N:11]([CH2:12][C:13]3[CH:14]=[C:15]([CH:24]=[CH:25][CH:26]=3)[O:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[S:42]([C:38]3[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=3)(=[O:44])=[O:43])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 57940794HCID 57940794, compound

Product 1

HCID 23729077Taprenepag isopropyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of isopropyl [3-({[4-(1H-pyrazol-1-yl)benzyl]amino}methyl)-phenoxy]acetate (0.28 g, 0.75 mmol), triethylamine (0.53 mL, 0.37 mmol) and pyridine-3-sulfonyl chloride (268 mg, 1.50 mmol) in dichloromethane (7 mL) was stirred at room temperature for 15 hours. The mixture was diluted with dichloromethane, and the combined organic layers were washed with water, brine and dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography (0-5% methanol in dichloromethane) afforded the desired product (180 mg, 69% based on the recovered amine starting material) as a pale yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29 (d, J=5.56 Hz, 6H) 4.37 (s, 2H) 4.42 (s, 2H) 4.50 (s, 2H) 5.06-5.25 (m, 1H) 6.49 (s, 1H) 6.65-6.75 (m, 2H) 6.77-6.84 (m, 1H) 7.17-7.23 (m, J=8.59 Hz, 3H) 7.46 (dd, J=7.83, 4.80 Hz, 1H) 7.60 (d, J=8.34 Hz, 2H) 7.74 (s, 1H) 7.92 (s, 1H) 8.08 (d, J=7.83 Hz, 1H) 8.83 (d, J=4.29 Hz, 1H) 9.09 (s, 1H). LRMS m/z calcd. for C27H28N4O5S ([M+H]+): 520.2. Found: 521.2.

Workup

  1. washthe combined organic layers were washed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a43bee8830e2467f83d28450551c8db3
Source dataset
uspto-grants-2009_11
Patent number
US07622475B2

Reaction notes

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