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 2097201Notes

Reaction equation

HRID 2097201 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

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-b9c184b6779b4c41b24a89782a6296dc
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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