1-Hydroxybenzotriazole hydrate → HCID 22612375, compound

HRID 844081Notes

Reaction equation

HRID 844081 reaction equation
OC(C1C=CC(C[N:10]2[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=O)[CH:11]2[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[CH:21]=2)=CC=1)(C)C.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([OH:45])([CH3:44])[CH3:43])=[CH:38][CH:37]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C>CN(C)C=O.O>[OH:45][C:42]([C:39]1[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:13](=[O:15])[C:12]2[CH:16]=[CH:17][CH:18]=[N:10][C:11]=2[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([OH:31])[C:27]([F:29])([F:28])[F:30])[CH:21]=2)=[CH:37][CH:38]=1)([CH3:44])[CH3:43]

Participants

7

Reactant 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 101542112-[4-(Aminomethyl)phenyl]propan-2-olHCID 21883477Ethylcarbodiimide hydrochlorideHCID 22612139HCID 22612139, compound

Product 1

HCID 22612375HCID 22612375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-[4-(1-Hydroxy-1-methyl-ethyl)-benzyl]-2-[3-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenoxy]-nicotinic acid (0.400 grams, 1.28 mmole), 2-(4-Aminomethyl-phenyl)-propan-2-ol (0.232 grams, 1.40 mmole), and 1-hydroxybenzotriazole hydrate (0.189 grams, 1.40 mmole) in dry dimethylformamide (5 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.294 grams, 1.54 mmole) and stirred over night. The mixture poured into 100 ml water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give an oil that was purified by chromatography on silica gel eluting with 2.5% methanol/methylene chloride (0.550 g). 1H NMR (CDCl3) d 1.54 (6H, s), 3.53 (1H, d), 4.66 (2H, d), 4.92 (1H, m), 7.46-7.15 (9H, m), 8.12 (1H, m), 8.16 (1H, dd) 8.62 (1H, dd). MW 313.25 MS (m/e) 313 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica gel eluting with 2.5% methanol/methylene chloride (0.550 g)

Sources & evidence

ORD record
ord-f9892c03198d4c858c57331c18ea773a
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…