Dimethylformamide → HCID 22612374, compound

HRID 844064Notes

Reaction equation

HRID 844064 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.O.ON1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2N=N1.Cl.C(N=[C:37]=[NH:38])C.C([O:42][CH2:43][CH3:44])(=O)C.[CH3:45]N(C)C=O>>[OH:42][C:43]([C:27]1[CH:32]=[CH:31][C:30]([CH2:37][NH:38][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]=2[O:7][C:6]2[CH:17]=[CH:18][CH:19]=[C:4]([O:3][C:2]([F:1])([F:21])[F:20])[CH:5]=2)=[CH:29][CH:28]=1)([CH3:44])[CH3:45]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochlorideHCID 22612256HCID 22612256, compound

Product 1

HCID 22612374HCID 22612374, compound

Procedure

A solution of 2-(3-Trifluoromethoxy-phenoxy)-nicotinic acid (0.409 grams, 1.366 mmole) 2-(4-Aminomethyl-phenyl)-propan-2-ol (0.200 grams, 1.24 mmole), and 1-hydroxybenzotriazole hydrate (0.185 grams, 1.366 mmole) in dry dimethylformamide was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.286 grams, 1.50 mmole) and stirred over night. The mixture was diluted ethyl acetate which was washed with water and brine, dried over MgSO4, filtered and concentrated to give an oil that was purified by chromatography on silica eluting with 3.5% methanol/methylene chloride to give an oil. (0.430 g). MS (m/e) 447 (M++1); 1H NMR (CDCl3) d 1.50 (6H, s), 4.70 (2H, d, J=5.81 Hz), 7.0-7.5 (9H, m), 8.00 (1H, bs), 8.20 (1H, m), 8.65 (1H, m).

Workup

  1. washwas washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oil that
  6. customwas purified by chromatography on silica eluting with 3.5% methanol/methylene chloride
  7. customto give an oil

Sources & evidence

ORD record
ord-e536cabc2f3f4136b4ed2294800d3ab9
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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