1-Hydroxybenzotriazole hydrate → HCID 22612322, compound

HRID 844079Notes

Reaction equation

HRID 844079 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[O:8][CH:9]1[N:17](CC2C=CC(C(O)(C)C)=CC=2)[CH:16]=[CH:15][CH:14]=[C:10]1[C:11]([OH:13])=O)=[O:4].[NH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([OH:44])([CH3:43])[CH3:42])=[CH:37][CH:36]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C>CN(C)C=O.O>[CH3:32][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[O:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([OH:44])([CH3:42])[CH3:43])=[CH:37][CH:36]=1)=[O:13])=[O:4]

Participants

7

Reactant 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 101542112-[4-(Aminomethyl)phenyl]propan-2-olHCID 21883477Ethylcarbodiimide hydrochlorideHCID 22612348HCID 22612348, compound

Product 1

HCID 22612322HCID 22612322, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(3-Dimethylcarbamoyl-phenoxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-nicotinic acid (0.300 grams, 1.05 mmole), 2-(4-Aminomethyl-phenyl)-propan-2-ol (0.190 grams, 1.15 mmole), and 1-hydroxybenzotriazole hydrate (0.155 grams, 1.15 mmole) in dry dimethylformamide (5 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.242 grams, 1.26 mmole) and stirred over night. The mixture poured into 100 ml water and extracted with ethyl acetate. The combined extracts were washed with 1 N NaOH, 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% methanollmethylene chloride (0.360 g). 1H NMR (CDCl3) d 1.54 (6H, s), 3.00 (3H, s), 3.08 (3H, s), 4.66 (2H, d), 7.20 (3H, m), 7.29 (4H, m), 7.43 (2H, m) 8.08 (1H, m), 8.18 (1H, dd), 8.63 (1H, dd); MS: m/e 433 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with 1 N NaOH, 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% methanollmethylene chloride (0.360 g)

Sources & evidence

ORD record
ord-c32f873ee1494b758c8dba615747dc13
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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