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 2097196Notes

Reaction equation

HRID 2097196 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-d0a7a53cf7e94abca99842882eec32c9
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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