Triethylamine → HCID 22046510, compound

HRID 1821767Notes

Reaction equation

HRID 1821767 reaction equation
C(OC([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[NH:30][C:31]([NH:33][C:34]2[CH:39]=[N:38][C:37]([CH3:40])=[CH:36][N:35]=2)=[O:32])[CH2:12]1)=O)C1C=CC=CC=1.C(N(CC)CC)C.[H][H]>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:40][C:37]1[N:38]=[CH:39][C:34]([NH:33][C:31]([NH:30][C:24]2[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=2[O:22][CH2:21][CH:13]2[CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:11][CH2:12]2)=[O:32])=[N:35][CH:36]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67256087HCID 67256087, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22046510HCID 22046510, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of the crude 3-{4-Methyl-2-[3-(5-methyl-pyrazin-2-yl)-ureido]-phenoxymethyl}-3,4dihydro-2H-quinoline-1-carboxylic acid benzyl ester (6.6 mg, 12 μmol) was heated in 5 mL EtOAc on a heat gun until in solution. The clear solution was cooled to rt and treated with triethylamine (3.4 μL, 24 μmol) followed by Pearlman's catalyst (20% palladium hydroxide on carbon, 9 mg). The mixture was put through a vacuum/purge cycle three times with hydrogen gas and then held under 1 atmosphere hydrogen pressure for 1 hour. The reaction was filtered through GF/F filter paper with EtOAc and concentrated to a white solid which corresponds to the desired product (4.7 mg, 100%). 1H-NMR (400 MHz, CDCl3/CD3OD) δ 8.23 (s, 1H), 8.18 (s, 1H), 7.96 (s, 1H), 7.04 (t, 1H), 6.97 (d, 1H), 6.81 (m, 2H), 6.67 (t, 1H),6.58 (d, 1H), 4.04 (m, 2H), 3.57 (d, 1H), 3.26 (t, 1H), 2.92 (ddd, 2H), 2.64 (m, 1H), 2.34 (s, 3H), 2.31 (s, 3H). LRMS (APCI, Positive) m/e 404.2 (M+1).

Workup

  1. filtrationThe reaction was filtered through GF/F
  2. filtrationfilter paper with EtOAc
  3. concentrationconcentrated to a white solid which

Sources & evidence

ORD record
ord-9337a31b26a04454932477b89d98ee84
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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