1-Hydroxybenzotriazole → ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1H-indole-2-carboxylate

HRID 239895Notes

Reaction equation

HRID 239895 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[NH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]2.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C:10]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]4)=[O:12])=[CH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 226453014-(Cyclopropylmethoxy)benzoic acid

Product 1

HCID 70967890ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1H-indole-2-carboxylateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(cyclopropylmethoxy)benzoic acid (576 mg), ethyl 5-amino-1H-indole-2-carboxylate (612 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (690 mg), 1-hydroxybenzotriazole (551 mg) and N,N-dimethylaminopyridine (367 mg) in DMF (20 mL) was stirred at room temperature for 2 hr. The reaction solution was extracted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue (brown solid) was washed with a small amount of ethyl acetate to give the title compound (820 mg, yield 72%).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe obtained residue (brown solid) was washed with a small amount of ethyl acetate

Sources & evidence

ORD record
ord-f19feb6894854c2691423afe4d868a59
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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