1-Hydroxybenzotriazole → HCID 19864522, compound

HRID 1199989Notes

Reaction equation

HRID 1199989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.[CH3:24][C:25]1[N:26]([CH2:34][CH2:35][CH2:36][CH2:37][NH2:38])[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[N:33]=1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:24][C:25]1[N:26]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:10](=[O:12])[CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:13])[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[N:33]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 2776723-(4-fluorophenyl)-3-oxopropanoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19864517HCID 19864517, compound

Product 1

HCID 19864522HCID 19864522, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold mixture of 3-(4-fluorophenyl)-3-oxoproprionic acid (prepared by standard saponification of the commercially available ester) (0.69 g), 1-hydroxybenzotriazole (0.56 g), and 4-(2-methylimidazo[4,5-c]pyrid-1-yl)butylamine (see Preparation 24) (0.71 g) in methylene chloride (20 cm3) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.8 g) over 5 minutes. The mixture was stirred at 0° for 1 hour and then at room temperature for 30 minutes, poured into 5% sodium bicarbonate solution (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were dried over Na2SO4, filtered and evaporated under vacuum. The residue was chromatographed on silica eluting with a methylene chloride/methanol mixture and the fractions containing the product were evaporated to give the title compound (0.82 g, 64%), which was used directly.

Workup

  1. waitat room temperature for 30 minutes
  2. extractionextracted with methylene chloride (3×50 ml)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on silica eluting with a methylene chloride/methanol mixture
  7. additionthe fractions containing the product
  8. customwere evaporated

Sources & evidence

ORD record
ord-5cf52ae22d2b43a8a3d54d6feef55a44
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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