Cyclopropylamine → HCID 21078792, compound

HRID 1375235Notes

Reaction equation

HRID 1375235 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.O>[CH:23]1([NH:26][C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:3]3[CH:4]=[C:5]([C:8]4[O:9][C:10]([CH3:13])=[N:11][N:12]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:15][CH:16]=2)=[O:21])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 69828Cyclopropylamine2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid

Product 1

HCID 21078792HCID 21078792, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (59 mg, 0.2 mmol), cyclopropylamine (11 mg, 0.2 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (0.2 mmol) were suspended in dry DCM (7 ml) and stirred at room temperature under nitrogen for 20 h. Cyclopropylamine (33 mg, 0.6 mmol) was added and the reaction stirred at room temperature for 21 h. 1-Hydroxybenzotriazole (27 mg, 0.2 mmol) was added and the reaction heated at 35° C. for 70 h. Water (10 ml) was added to the cooled reaction, and the organic fraction separated. The organic phase was absorbed onto a silica flash column and eluted with DCI/ethanol/ammonia (300:8:1). Solvent was evaporated from the product fractions under vacuum to give N-(cyclopropyl)-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide (26 mg, 39%).

Workup

  1. stirringthe reaction stirred at room temperature for 21 h
  2. temperaturethe reaction heated at 35° C. for 70 h
  3. customthe organic fraction separated
  4. customThe organic phase was absorbed onto a silica flash column
  5. washeluted with DCI/ethanol/ammonia (300:8:1)
  6. customSolvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record
ord-cf5ce60c368a4c48b837c8a10a601a1c
Source dataset
uspto-grants-2007_01
Patent number
US07166623B2

Reaction notes

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