1,2-Dichloroethane → HCID 16661276, compound

HRID 1362425Notes

Reaction equation

HRID 1362425 reaction equation
C(Cl)CCl.[CH3:5][NH:6][CH2:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[CH:12][CH:11]=2.Cl.[O:19]=[C:20]1[CH2:25][O:24][C:23]2[CH:26]=[C:27](/[CH:30]=[CH:31]/[C:32](O)=[O:33])[CH:28]=[N:29][C:22]=2[NH:21]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:5][N:6]([CH2:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:32](=[O:33])/[CH:31]=[CH:30]/[C:27]1[CH:28]=[N:29][C:22]2[NH:21][C:20](=[O:19])[CH2:25][O:24][C:23]=2[CH:26]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 26722512N-Methyl-1-(3-methyl-1H-indol-2-YL)methanamineHCID 66967073(E)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride

Product 1

HCID 16661276HCID 16661276, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (149 mg, 1.3 mmol) was added to a solution of N-methyl(3-methyl-1H-indol-2-yl)methanamine (110 mg, 1.0 mmol), (E)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride (220 mg, 1.1 mmol), HOBT.H2O (81 mg, 1.0 mmol) and DIPEA (0.43 mL, 3.0 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 (12 mg, 4%). 1H NMR (300 MHz, DMSO-d6) δ 8.25 (s, 1H), 7.97 (s, 1H), 7.77 (d, J=7.1 Hz, 1H), 7.60 (s, 1H), 7.45 (d, J=7.4 Hz, 1H), 7.34 (m, 2H), 7.18 (s, 1H), 7.11 (m, 1H), 4.90-4.79 (rotamers, s, 2H), 4.72 (s, 2H), 4.60 (s, 3H), 2.31 (s, 3H); MS (ESI): mile 377.2 (C21H20N4O3+H)+.

Workup

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

Sources & evidence

ORD record
ord-18d1377eddb04b20a4841923a864819a
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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