Indomethacin → HCID 9849567, compound

HRID 2219664Notes

Reaction equation

HRID 2219664 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20](O)=[O:21])=[C:9]2[CH3:23])=[O:7])=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:48]1([NH:54][CH:55]2[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]2)[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:55]1([N:54]([CH:48]2[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]2)[C:20](=[O:21])[CH2:19][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:9]=2[CH3:23])[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]1

Participants

6

Reactant 4

HCID 3715IndomethacinHCID 7582DicyclohexylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 9849567HCID 9849567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a flask was added 0.180 g (0.5 mmol) of 1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid, 1.8 mL of anhydrous dichloromethane, 0.194 g (0.6 mmol) of TBTU (o-benzotriazol-1-yl-N,N,N′,N′,-tetramethyluronium tetrafluoroborate), 0.066 mL (0.6 mmol) of dicyclohexylamine and finally 0.22 mL (1.26 mmol) of diisopropylethyl amine. The reaction was stirred at room temperature for 20 hr then diluted with more dichloromethane (10 mL). The solution was washed with dilute aqueous citric acid (2×10 mL), aqueous sodium bicarbonate (10 mL) and water (10 mL) before drying (MgSO4), filtering and evaporating the filtrate. The residue was slurried with a hexanes/ethyl acetate mix to give the title compound. 1H NMR (CDCl3) δ 7.56 (2H, d), 7.40 (2H, d), 7.01 (1H, bs), 6.61 (1H, d), 6.56 (1H, dd), 3.75 (3H, s), 3.63 (2H, s), 3.41 (1H, m), 2.73 (1H, b), 2.38 (3H, s), 0.9-1.8 (20H, m) Mass Spectrum m/e 521/523 (M+1).

Workup

  1. washThe solution was washed with dilute aqueous citric acid (2×10 mL), aqueous sodium bicarbonate (10 mL) and water (10 mL)
  2. dry with materialbefore drying (MgSO4)
  3. filtrationfiltering
  4. customevaporating the filtrate
  5. additionmix

Sources & evidence

ORD record
ord-4911afe2c910441f888f13196cd511fb
Source dataset
uspto-grants-2008_08
Patent number
US07414067B2

Reaction notes

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