Triethylamine → HCID 24794585, compound

HRID 2246593Notes

Reaction equation

HRID 2246593 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]([N:13]([CH3:15])[CH3:14])[CH2:9][C@H:8]2[NH:16][C:17](=[O:19])[CH3:18])[C:3]1=[O:20].Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=2)[N:25]=[CH:24][N:23]=1.C(N(CC)CC)C>C(O)(C)C>[CH3:14][N:13]([CH3:15])[C@H:10]1[CH2:9][C@@H:8]([NH:16][C:17](=[O:19])[CH3:18])[C@@H:7]([N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:32]([F:34])([F:35])[F:33])[CH:30]=4)[N:25]=[CH:24][N:23]=3)[C:3]2=[O:20])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 210750954-Chloro-6-(trifluoromethyl)quinazolineHCID 68567035HCID 68567035, compound

Product 1

HCID 24794585HCID 24794585, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(dimethylamino)cyclohexyl)acetamide (40 mg, 0.14 mmol) in isopropanol (6 mL) was added 4-chloro-6-(trifluoromethyl)quinazoline (39 mg, 0.17 mmol) and triethylamine (0.02 mL, 0.14 mmol). The mixture was stirred at RT for 16 h and concentrated in vacuo to a crude oil, which was purified by semi-preparative reverse phase HPLC (gradient elution, water/methanol/TFA) to give the title compound (70 mg, 71% yield). LC/MS found [M+H]+=479. 1H-NMR (400 MHz, CD3OD), δ ppm: 8.87 (s, 1H), 8.72 (s, 1H), 8.22 (m, 1H), 7.87 (m, 1H), 5.49 (m, 1H), 4.23 (m, 1H), 4.2 (m, 1H), 4.12 (m, 1H), 3.75 (m, 1H), 3.65 (m, 1H), 3.38 (m, 1H), 2.82 (s, 6H), 2.51 (m, 1H), 2.35 (m, 1H), 2.15 (m, 1H), 2.14-1.86 (m, 5H), 1.84 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo to a crude oil, which
  2. customwas purified by semi-preparative reverse phase HPLC (gradient elution, water/methanol/TFA)

Sources & evidence

ORD record
ord-76c2b6dc636f4202bf447f01ca680287
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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