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

HRID 51960Notes

Reaction equation

HRID 51960 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 1N 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 1N 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-9d9ead93c2444ffc9ab36db326346697
Source dataset
uspto-grants-2004_03
Patent number
US06713489B2

Reaction notes

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