1-Hydroxybenzotriazole → HCID 57901820, compound

HRID 1851491Notes

Reaction equation

HRID 1851491 reaction equation
Cl.[C:2]([S:21][CH2:22][CH2:23][NH2:24])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[C:34]([NH:36][S:37]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)(=[O:39])=[O:38])[CH:35]=1)[NH:32][C:31]([C:45](O)=[O:46])=[CH:30]2.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[C:34]([NH:36][S:37]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)(=[O:39])=[O:38])[CH:35]=1)[NH:32][C:31]([C:45]([NH:24][CH2:23][CH2:22][S:21][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:46])=[CH:30]2

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 57901602HCID 57901602, compound

Product 1

HCID 57901820HCID 57901820, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(tritylthio)ethylamine hydrochloride (0.32 g), triethylamine (0.126 mL) and N,N-dimethylformamide (10 mL) were added 5-methoxy-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (265 mg), 1H-1,2,3-benzotriazol-1-ol (0.15 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (188 mg) under ice-cooling, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained oil was crystallized from dichloromethane-hexane to give the title compound (465 mg, yield 95%) as pale-yellow crystals. melting point 128-129° C.

Workup

  1. temperaturecooling
  2. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained oil was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-4a9195f183664eb9812aab80f133c7cf
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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