1,2-Dichloroethane → (e)-n-((7-Ethyl-3-methyl-1h-indol-2-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide

HRID 1362447Notes

Reaction equation

HRID 1362447 reaction equation
[CH2:1](Cl)CCl.[CH3:5][CH2:6][C:7]1[C:12]2[NH:13][C:14]([CH2:17][NH2:18])=[C:15]([CH3:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1.Cl.[O:20]=[C:21]1[CH2:26][O:25][C:24]2[CH:27]=[C:28](/[CH:31]=[CH:32]/[C:33]([OH:35])=O)[CH:29]=[N:30][C:23]=2[NH:22]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:6]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:12]=1[NH:13][C:14]([CH2:17][N:18]([CH3:1])[C:33](=[O:35])/[CH:32]=[CH:31]/[C:28]1[CH:29]=[N:30][C:23]3[NH:22][C:21](=[O:20])[CH2:26][O:25][C:24]=3[CH:27]=1)=[C:15]2[CH3:16])[CH3:5]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66967073(E)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochlorideHCID 66967213(7-Ethyl-3-methyl-1h-indol-2-yl)-n-methanamine

Product 1

HCID 16661575(e)-n-((7-Ethyl-3-methyl-1h-indol-2-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamideYield 12.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (147 mg, 0.7 mmol) was added to a solution of (7-ethyl-3-methyl-1H-indol-2-yl)-N-methanamine (108.7 mg, 0.5 mmol), (E)-3-(3-oxo-3,4,dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride (151 mg, 0.6 mmol), HOBT.H2O (73 mg, 0.5 mmol) and DIPEA (0.39 mL, 2.1 mmol) in dry DMF (5 mL). After stirring overnight, water was added. The precipitate that formed was washed with ethyl acetate and dried to afford the title compound (25 mg, 0.001%). 1H NMR (400 MHz, DMSO-d6) δ 9.34 (s, 1H), 8.92 (s, 1H), 8.15 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.41 (s, 1H), 7.38 (d, J=7.2 Hz, 1H), 7.05 (m, 2H), 6.80 (d, J=7.5 Hz, 1H), 4.70 (s, 2H), 3.15 (s, 3H), 2.88 (q, J=7.0 Hz, 2H), 2.40 (s, 3H), 1.30 (t, J=7.2 Hz, 3H); MS (ESI): m/e 405.2 (C23H24N4O3+H)+.

Workup

  1. customThe precipitate that formed
  2. washwas washed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-d67ad3808e9c471ab5209b78466b0312
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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