1-Hydroxybenzotriazole → HCID 21078782, compound

HRID 1375248Notes

Reaction equation

HRID 1375248 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.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.[NH2:45][CH:46]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:47]([NH:49][CH3:50])=[O:48]>CN(C=O)C>[CH3:52][C:51]([CH3:54])([CH3:53])[CH:46]([NH:45][C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:3]2[CH:4]=[C:5]([C:8]3[O:9][C:10]([CH3:13])=[N:11][N:12]=3)[CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:19][CH:18]=1)=[O:21])[C:47]([NH:49][CH3:50])=[O:48]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 34964452-Amino-N,3,3-TrimethylbutanamideHCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid

Product 1

HCID 21078782HCID 21078782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (11.3 mg, 0.034 mmol), HOBT (6.0 mg, 0.044 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (8.0 mg, 0.042 mmol) and 2-amino-N,3,3-trimethylbutanamide (0.34 mmol) were mixed in DMF (0.7 ml) and the reaction left at room temperature for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (0.4 ml) and water (0.4 ml). The organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml) and the DCM evaporated under vacuum. The residue was purified by mass directed HPLC to give N-[2,2-dimethyl-1-(methylaminocarbonyl)propyl]-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide.

Workup

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (0.4 ml) and water (0.4 ml)
  3. washThe organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml)
  4. customthe DCM evaporated under vacuum
  5. customThe residue was purified by mass

Sources & evidence

ORD record
ord-ad35f1102b964cbc9812d53ed49f5402
Source dataset
uspto-grants-2007_01
Patent number
US07166623B2

Reaction notes

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