Potassium Carbonate → HCID 11234522, compound

HRID 347280Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][NH:13][C:14](=[O:22])[C@@H:15]([NH2:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][CH2:5]2.Cl[C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][NH:13][C:14](=[O:22])[C@@H:15]([NH:21][C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1)[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 240 °C

Procedure

(S)-2-Amino-4,4-dimethyl-pentanoic acid [2-(5-fluoro-2,3-dihydro-indol-1-yl)-ethyl]-amide (20 mg, 0.066 mmol) was dissolved in DMF (0.7 mL) containing equimolar amounts of 2-chloropyrazine (6 μL, 0.066 mmol), 0.1 equivalents of CuI (1.3 mg, 0.006 mmol), and 1.5 equivalents of potassium carbonate (13.9 mg, 0.099 mmol). The mixture was stirred and heated by microwave to 240° C. for 30 minutes. After completion the mixture was purified by reverse phase LC to afford (S)-4,4-Dimethyl-2-(pyrazin-2-ylamino)-pentanoic acid [2-(5-fluoro-2,3-dihydro-indol-1-yl)-ethyl]-amide 2 (8.3 mg, 0.02 mmol, 32%): 1H-NMR (400 MHz, CD3OD) δ=8.37 (m, 2H), 6.82–6.41 (m, 4H), 4.57 (dd, J=9.2, J=3.2, 1H), 3.42 (t, J=6.2, 2H), 3.36 (t, J=8.2, 2H), 3.14 (m, 2H), 2.88 (t, J=8.2, 2H), 1.83–1.62 (m, 2H), 0.96 (s, 9H). MS calcd. for C21H29FN5O (M+H+) 386.23. found 386.5.

Workup

customAfter completion the mixture was purified by reverse phase LC

Sources & evidence

ORD record: ord-5f83ea28729544dbbb67708aa0dc204a
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173051B2

Reaction notes

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