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1-Hydroxybenzotriazole → HCID 178489632, compound

HRID 504870
Notes
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Reaction equation

HRID 504870 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]([CH3:31])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]1[S:23][CH:24]([CH2:27][C:28](O)=[O:29])[CH2:25][N:26]=1)=[CH:18]2)(=[O:11])=[O:10].N[N:33]1[CH:37]=[N:36][CH:35]=[N:34]1.[N:38]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]([CH3:31])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]1[S:23][CH:24]([CH2:27][C:28]([NH:38][C:35]3[NH:36][CH:37]=[N:33][N:34]=3)=[O:29])[CH2:25][N:26]=1)=[CH:18]2)(=[O:10])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117080471H-1,2,4-triazol-1-amineHCID 59135901(2-{7-[[(2-methoxyphenyl)sulfonyl](methyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid

Product 1

HCID 178489632HCID 178489632, compound
Yield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (2-{7-[[(2-methoxyphenyl)sulfonyl](methyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (150 mg), 2-amino-1,2,4-triazole (36 mg), 1H-1,2,3-benzotriazol-1-ol (67 mg) and N,N-dimethylformamide (8 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (94 mg) under ice-cooling, and the mixture was stirred from under ice-cooling to room temperature for 15 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:methanol=100:0-95:5), and the obtained colorless oil was crystallized from ethyl acetate-hexane to give the title compound (118 mg, yield 69%) as colorless prism crystals. MS: 526 (MH+). melting point 208-209° C.

Workup

  1. temperaturecooling
  2. washwashed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained colorless oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e18fc0a1a4254fb38d1a76bd382630bf
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07777047B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes