Triethylamine → HCID 24794622, compound

HRID 2246611Notes

Reaction equation

HRID 2246611 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@@H:10]([O:13][CH3:14])[CH2:9][C@H:8]2[CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:3]1=[O:20].C(N(CC)CC)C.Cl[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:39]([F:42])([F:41])[F:40])[CH:37]=2)[N:32]=[CH:31][N:30]=1>CC(O)C>[CH3:14][O:13][C@H:10]1[CH2:9][C@@H:8]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C@@H:7]([N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[C:36]([C:39]([F:41])([F:42])[F:40])[CH:37]=4)[N:32]=[CH:31][N:30]=3)[C:3]2=[O:20])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 210750954-Chloro-6-(trifluoromethyl)quinazolineHCID 68564795HCID 68564795, compound

Product 1

HCID 24794622HCID 24794622, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A sample of the N-(((1S,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-methoxycyclohexyl)methyl)acetamide (220 mg, 0.776 mmol) was dissolved in 2-propanol (10 ml) at room temperature. To this solution was added triethylamine (0.433 ml, 3.11 mmol), followed by 4-chloro-6-(trifluoromethyl)quinazoline (235 mg, 1.009 mmol). The reaction mixture was stirred overnight. It was concentrated and chromatographed (120 g silica gel eluting with 5% followed by 10% MeOH in CH2Cl2) to afford the title compound (300 mg, 0.626 mmol, 81% yield) as a white solid. LC/MS found [M+H]+=480.4. 1H-NMR (400 MHz, CDCl3), δ ppm: 8.6 (s, 1H), 8.51 (s, 1H), 7.92 (br s, 1H), 7.87-7.82 (m, 2H), 6.28 (br s, 1H), 5.00 (dd, J=16.02, 8.65 Hz, 1H), 4.36-4.35 (m, 1H), 3.72-3.68 (m, 1H), 3.63-3.56 (m, 1H), 3.37-3.23 (m, 2H), 3.31 (s, 3H), 3.18-3.13 (m, 1H), 2.69-2.66 (m, 1H), 2.12-2.07 (m, 1H), 2.06-1.89 (m, 4H), 1.96 (s, 3H), 1.74-1.67 (m, 1H), 1.57-1.51 (m, 1H), 1.30-1.28 (m, 1H).

Workup

  1. concentrationIt was concentrated
  2. customchromatographed (120 g silica gel eluting with 5% followed by 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-bcc89b429f53425abf9e8ee833973396
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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