Isopropylamine → HCID 49804465, compound

HRID 1807489Notes

Reaction equation

HRID 1807489 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH3:20])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>>[CH:22]([NH:25][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH3:20])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1)([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 66643579HCID 66643579, compound

Product 1

HCID 49804465HCID 49804465, compoundYield 30%

Procedure

A mixture of 6-(5-methyl-3-propyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (290 mg, 1.0 mmol), isopropylamine (71 mg, 1.2 mmol) and TBD (42 mg, 0.30 mmol) was stirred for 15 h at ambient temperature under argon. The reaction mixture was concentrated onto silica then purified by chromatography (silica, 0 to 60% ethyl acetate in heptane) to give the title compound (95 mg, 30%) as a white solid after trituration with diisopropyl ether. MS: m/e=318.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated onto silica
  2. customthen purified by chromatography (silica, 0 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-73fd897f2a0546a68087698b8a6d606a
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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