Triethylamine → [r]-7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid (1-pyridin-2-yl-propyl)-amide

HRID 841823Notes

Reaction equation

HRID 841823 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=2[C:11]([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:24](O)=[O:25])[CH:20]=[N:21]3)=[CH:16][CH:15]=2)=[O:12])=[N:7][CH:8]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C@H:39]([NH2:42])[CH2:40][CH3:41].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C@H:39]([NH:42][C:24]([C:19]1[CH:20]=[N:21][C:22]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([NH:13][C:11](=[O:12])[C:10]1[CH:27]=[CH:28][CH:29]=[CH:30][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:31])[F:32])=[CH:8][N:7]=1)[CH:23]=2)=[O:25])[CH2:40][CH3:41]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227368887-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acidHCID 28064429(R)-1-(pyridin-2-yl)propan-1-amine

Product 1

HCID 70160859[r]-7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid (1-pyridin-2-yl-propyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-[2-(5-Trifluoromethyl-pyridin-2-yl)-benzoylamino]-quinoline-3-carboxylic acid (25 mg, 0.06 mmol), [R]-1-pyridin-2-yl-propylamine (23 mg, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (33 mg, 0.17 mmol), 1-hydroxybenzotriazole (23 mg, 0.17 mmol), and triethylamine (69 mg, 0.69 mmol) were combined in 5 ml of dichloromethane. After stirring 5 h at room temperature, the mixture was diluted with dichloromethane and washed with 10 ml of 1 N HCl, the organic layer was dried (magnesium sulfate), filtered and concentrated under vacuum. Purification of the residue by silica gel chromatography eluting with 5% methanol in ethyl acetate afforded the title compound.

Workup

  1. washwashed with 10 ml of 1 N HCl
  2. dry with materialthe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification of the residue by silica gel chromatography
  6. washeluting with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-58e92a822b1f4485a67e359f5d99bfe0
Source dataset
uspto-grants-2002_04
Patent number
US06369075B1

Reaction notes

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