1,2-Dichloroethane → (E)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-((3-vinyl-1H-indol-2-yl)methyl)acrylamide

HRID 1362438ノート

反応式

HRID 1362438 の反応式
C(Cl)CCl.[CH3:5][NH:6][CH2:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH:17]=[CH2:18])=[CH:14][CH:13]=[CH:12][CH:11]=2.Cl.[O:20]=[C:21]1[CH2:26][O:25][C:24]2[CH:27]=[C:28](/[CH:31]=[CH:32]/[C:33](O)=[O:34])[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>[CH3:5][N:6]([CH2:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH:17]=[CH2:18])=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:33](=[O:34])/[CH:32]=[CH:31]/[C:28]1[CH:29]=[N:30][C:23]2[NH:22][C:21](=[O:20])[CH2:26][O:25][C:24]=2[CH:27]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59277599N-methyl(3-vinyl-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

生成物 1

HCID 16661420(E)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-((3-vinyl-1H-indol-2-yl)methyl)acrylamide収率 23.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

EDC (73 mg, 0.3 mmol) was added to a solution of N-methyl(3-vinyl-1H-indol-2-yl)methanamine (54.7 mg, 0.29 mmol), (E)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride (79 mg, 0.3 mmol), HOBT.H2O (39 mg, 0.29 mmol) and DIPEA (0.21 mL, 1.1 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 (26 mg, 23%). 1H NMR (400 MHz, DMSO-d6) δ 11.41 (s, 1H), 11.20-11.05 (rotamers, s, 1H), 8.18 (s, 1H), 7.87 (s, 1H), 7.80 (d, J=7.8 Hz, 1H), 7.51 (d, J=15.6 Hz, 1H), 7.38 (d, J=7.7 Hz, 1H), 7.22 (d, J=15.6 Hz, 1H), 7.10 (t, J=7.1 Hz, 1H), 7.07-6.98 (m, 2H), 5.62 (d, J=17.9 Hz, 1H), 5.12 (d, J=11.0 Hz, 1H), 5.03 (s, 2H), 4.68 (s, 3H), 3.09 (s, 2H); MS (ESI): m/e 389.1 (C22H20N4O3+H)+.

後処理

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

出典と根拠

ORDレコード
ord-01eec6fb3c5d47139370b3df23b74985
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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