Diisopropylethylamine → HCID 68651123, compound

HRID 646764Notes

Reaction equation

HRID 646764 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]Br)[CH:9]=2)=[CH:6][N:7]=1.[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([F:31])[CH:30]=1)[C@@H:27]([NH2:32])[CH2:26][CH2:25]2.C(N(C(C)C)CC)(C)C>C(#N)C>[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:32][CH:27]3[C:28]4[C:24](=[CH:23][C:22]([F:21])=[CH:30][C:29]=4[F:31])[CH2:25][CH2:26]3)[CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68650253(1S)-5,7-Difluoro-2,3-dihydro-1H-inden-1-amineHCID 68651040HCID 68651040, compound

Product 1

HCID 68651123HCID 68651123, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 3-Amino-6-[3-(bromomethyl)phenyl]-N-ethylpyrazine-2-carboxamide (100 mg, 1.0 eq) was dissolved in acetonitrile (5 mL) and treated with [(1S)-5,7-difluoro-2,3-dihydro-1H-inden-1-yl]amine (151 mg, 3.0 eq), diisopropylethylamine (62 mg, 1.6 eq) at ambient temperature. After being stirred for 8 h, the white suspension was concentrated in vacuo and purified by flash column chromatography to give the title compound as colorless oil, which was dissolved in ethyl acetate (10 mL) and treated 1M HCl in ether. The resulting precipitate was filtered, washed with ether (2×2mL), and dried to afford 42mg (12% yield) of 3-amino-6-(3-{[(5,7-difluoro-2,3-dihydro-1H-inden-1-yl)amino]methyl}phenyl)-N-ethylpyrazine-2-carboxamide hydrochloride as a yellow solid: 1H NMR (400 MHz, CD3OD): δ 8.71 (s, 1H), 8.22 (s, 1H), 8.13 (d, 1H), 7.57 (t, 1H), 7.51 (m, 1H), 7.06 (m, 1H), 6.98 (m, 1H), 5.08 (m, 1H), 4.38 (q, 2H), 3.45 (m, 2H), 3.39 (m, 1H), 3.05 (m, 1H), 2.84 (m, 1H), 2.53 (m, 1H); MS (FI) for C23H23NSOF2: 424.16 (MH+).

Workup

  1. concentrationthe white suspension was concentrated in vacuo
  2. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-656d4bb8f4854f779da56fd2344e9f29
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…