1-Hydroxybenzotriazole → HCID 19024865, compound

HRID 249174Notes

Reaction equation

HRID 249174 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]([CH:16]([C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH:50]([CH3:52])[CH3:51])=[CH:45][CH:44]=1)[O:17][C:18]1[CH:42]=[CH:41][C:21]([C:22]([C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:25]=2)=[O:23])=[CH:20][CH:19]=1)([OH:15])=O.[CH2:53]([C:57]1[CH:63]=[CH:62][C:60]([NH2:61])=[CH:59][CH:58]=1)[CH:54]([CH3:56])[CH3:55].ON1C2C=CC=CC=2N=N1>ClCCl>[CH2:49]([C:46]1[CH:47]=[CH:48][C:43]([CH:16]([C:13](=[O:15])[NH:61][C:60]2[CH:62]=[CH:63][C:57]([CH2:53][CH:54]([CH3:56])[CH3:55])=[CH:58][CH:59]=2)[O:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:25]=3)=[O:23])=[CH:41][CH:42]=2)=[CH:44][CH:45]=1)[CH:50]([CH3:51])[CH3:52]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1216274-IsobutylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19024864HCID 19024864, compound

Product 1

HCID 19024865HCID 19024865, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (30 mg) was added to a mixture of ethyl 4-[3-[4-[(carboxy)(4-isobutylphenyl)methoxy]benzoyl]-indol-1-yl]butyrate (70 mg), 4-isobutylaniline (20 mg) and 1-hydroxybenzotriazole (20 mg) in dichloromethane (3 ml). After stirred at 25° C. for 4 hours, the mixture was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (5 g) eluting with chloroform to give ethyl 4-[3-[4-[(4-isobutylphenyl)[(4-isobutylphenyl)carbamoyl]methoxy]benzoyl]indol-1-yl]butyrate (85 mg) as an oil.

Workup

  1. customthe mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (5 g)
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-e2326a7dded74f09bdc92435593d449e
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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