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1,2-Dichloroethane → (e)-n-((3,6-Dimethyl-1h-indol-5-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-yl)acrylamide

HRID 1362452
Notes
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Reaction equation

HRID 1362452 reaction equation
[CH2:1](Cl)[CH2:2]Cl.CC[C:7]1[C:12]2[NH:13][C:14](CN)=[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](/C=C/C(O)=O)[CH:29]=[N:30][C:23]=2[NH:22]1.[CH3:36][CH2:37]N(C(C)C)C(C)C.[CH3:45][N:46]([CH:48]=[O:49])C>O>[CH3:16][C:15]1[C:11]2[C:12](=[CH:7][C:1]([CH3:2])=[C:9]([CH2:8][N:46]([CH3:45])[C:48](=[O:49])/[CH:36]=[CH:37]/[CH:26]3[O:25][C:24]4[CH:27]=[CH:28][CH:29]=[N:30][C:23]=4[NH:22][C:21]3=[O:20])[CH:10]=2)[NH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 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 87218141
(e)-n-((3,6-Dimethyl-1h-indol-5-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-yl)acrylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

EDC (198 mg, 1.0 mmol) was added to a solution of (7-ethyl-3-methyl-1H-indol-2-yl)-N-methanamine (150 mg, 0.8 mmol), (E)-3-(3-oxo-3,4,dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride (224 mg, 0.87 mmol) HOBT.H2O (107 mg, 0.8 mmol) and DIPEA (0.57 mL, 3.1 mmol) in dry DMF (5 mL). After heating overnight, water was added. The precipitate that formed was washed with ethyl acetate and dried (184 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ, 11.42 (s, 1H), 10, 45 (s, 1H), 8.24-8.05 (rotamers, s, 1H), 7.98-7.80 (rotamers, s, 2H), 7.54 (d, J=7.4 Hz, 1H), 7.24 (m, 1H), 7.14 (m, 1H), 6.98 (s, 1H), 4.90-4.78 (rotamers, s, 2H), 3.05 (s, 2H), 2.84 (s, 3H), 2.45 (s, 3H), 2.31 (s, 3H); m/e 391.1 (C22H22N4O3+H)+.

Workup

  1. temperatureAfter heating overnight
  2. customThe precipitate that formed
  3. washwas washed with ethyl acetate
  4. customdried (184 mg, 59%)

Sources & evidence

ORD record
ord-ecd02fc503624b6b86e45034152f1674
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879872B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes