1-Hydroxybenzotriazole → HCID 68458881, compound

HRID 1994971Notes

Reaction equation

HRID 1994971 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([N:21]([CH3:31])[S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)(=[O:24])=[O:23])[CH:20]=1)[NH:17][C:16]([C:32]1[S:33][CH:34]([CH2:37][C:38](O)=[O:39])[CH2:35][N:36]=1)=[CH:15]2.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O.C(N(CC)CC)C>[OH:6][CH:4]1[CH2:5][N:2]([C:38](=[O:39])[CH2:37][CH:34]2[S:33][C:32]([C:16]3[NH:17][C:18]4[C:14]([CH:15]=3)=[CH:13][C:12]([O:11][CH2:10][CH2:9][O:8][CH3:7])=[CH:20][C:19]=4[N:21]([CH3:31])[S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)(=[O:23])=[O:24])=[N:36][CH2:35]2)[CH2:3]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27592903-Hydroxyazetidine hydrochlorideHCID 68461826HCID 68461826, compound

Product 1

HCID 68458881HCID 68458881, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of azetidin-3-ol hydrochloride (80 mg), triethylamine (75 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 15 min. (2-{5-(2-Methoxyethoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (250 mg), 1H-1,2,3-benzotriazol-1-ol (100 mg) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (140 mg) were added to the reaction mixture, and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-methanol (100:0-95:5, volume ratio) to give the title compound (80 mg, yield 29%) as a colorless amorphous solid.

Workup

  1. additionwere added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluted with ethyl acetate-methanol (100:0-95:5, volume ratio)

Sources & evidence

ORD record
ord-36bd56784c5f45899f846ee4b750faf3
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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