Diisobutylamine → HCID 53673021, compound

HRID 1857604Notes

Reaction equation

HRID 1857604 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([C:27](O)=[O:28])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.[CH2:50]([NH:54][CH2:55][CH:56]([CH3:58])[CH3:57])[CH:51]([CH3:53])[CH3:52].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([C:27](=[O:28])[N:54]([CH2:55][CH:56]([CH3:58])[CH3:57])[CH2:50][CH:51]([CH3:53])[CH3:52])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8085DiisobutylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22124479HCID 22124479, compound

Product 1

HCID 53673021HCID 53673021, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[2-(1-tert-butoxycarbonyl-piperidin-2-yl)-ethoxy]-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinoline-6-carboxylic acid (48 mg in 0.50 mL methylene chloride) was added 12 mg 1-hydroxybenzotriazole (HOBt) followed by 0.020 mL diisobutylamine, 0.025 mL triethylamine and 33 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and the mixture stirred at room temperature. After 22 hours, the mixture was diluted with methylene chloride and washed with 10% aqueous sodium bisulfate and brine. The organics were dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (chloroform:methanol, 97.5:2.5) to give the title compound (37 mg).

Workup

  1. washwashed with 10% aqueous sodium bisulfate and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. customthe concentrate purified by flash chromatography on silica gel (chloroform:methanol, 97.5:2.5)

Sources & evidence

ORD record
ord-b17898b6c950478ea2124d9d641cb698
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

Loading…