1-Hydroxybenzotriazole → HCID 11955377, compound

HRID 1610492Notes

Reaction equation

HRID 1610492 reaction equation
[NH2:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:23]=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][CH3:20])[CH:13]=2)=[CH:7][CH:6]=1)[OH:4].[C:35]1([C:46](O)=[O:47])[CH:36]=[CH:37][CH:38]=[C:39]2[CH2:45][CH2:44][CH2:43][CH:42]=[CH:41][C:40]=12.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(#N)C.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH:2]([NH:1][C:46]([C:35]3[CH:36]=[CH:37][CH:38]=[C:39]4[CH2:45][CH2:44][CH2:43][CH:42]=[CH:41][C:40]=34)=[O:47])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:23]=3)=[CH:6][CH:7]=2)=[CH:13][C:14]=1[CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22261864HCID 22261864, compoundHCID 222620106,7-dihydro-5H-benzo[a]cycloheptene-1-carboxylic acid

Product 1

HCID 11955377HCID 11955377, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (1RS,2SR)-2-amino-1-(4-((4-chloro-3-ethylphenyl)oxy)phenyl)-3-(3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)-1-propanol (300 mg, 0.60 mmol) in acetonitrile (16 ml) were added 6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxylic acid (114 mg, 0.60 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (174 mg, 0.91 mmol) and 1-hydroxy-1H-benzotriazole (92 mg, 0.60 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed successively with 1N hydrochloric acid, 1N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave the title compound (318 mg, 79%).

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed successively with 1N hydrochloric acid, 1N aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9be4f3e5cfaf46cdb84601d064d794d7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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