1,2-Dichloroethane → (e)-n-((3,7-Dimethyl-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 2097177Notes

Reaction equation

HRID 2097177 reaction equation
[CH2:1](Cl)[CH2:2]Cl.Cl.[O:6]=[C:7]1[CH2:12][O:11][C:10]2[CH:13]=[C:14](/[CH:17]=[CH:18]/[C:19]([OH:21])=O)[CH:15]=[N:16][C:9]=2[NH:8]1.[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=[N:28][C:26]=2[CH:27]=1.CC[N:34]([CH:38]([CH3:40])C)[CH:35](C)C.[CH3:41]N(C=O)C>O>[CH3:1][C:2]1[C:27]2[C:26](=[C:25]([CH3:41])[CH:24]=[CH:23][CH:22]=2)[NH:28][C:40]=1[CH2:38][N:34]([CH3:35])[C:19](=[O:21])/[CH:18]=[CH:17]/[C:14]1[CH:15]=[N:16][C:9]2[NH:8][C:7](=[O:6])[CH2:12][O:11][C:10]=2[CH:13]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66967073(E)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride

Product 1

HCID 16661277(e)-n-((3,7-Dimethyl-1h-indol-2-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

EDC (157 mg, 0.8 mmol) was added to a solution of (3,7-dimethyl-1H-indol-2-yl)-N-methanamine (120 mg, 0.6 mmol), (E)-3-(3-oxo-3,4,dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride (177 mg, 0.7 mmol), HOBT.H2O (85 mg, 0.6 mmol) and DIPEA (0.45 mL, 2.5 mmol) in dry DMF (5 mL). After stirring overnight, water was added. The precipitate that formed was washed with ethyl acetate and dried (14 mg, 6%). 1H NMR (400 MHz, DMSO-d6) δ 11.41 (s, 1H), 10.60-10.52 (rotamers, s, 1H), 8.19 (s, 1H), 7.87 (s, 1H), 7.50 (d, J=7.6 Hz, 1H), 7.25 (d, J=6.8 Hz, 1H), 6.88 (m, 2H), 4.90-4.77 (rotamers, s, 2H), 4.68 (s, 3H), 3.05 (s, 2H), 2.84 (s, 1H), 2.44 (s, 3H), 2.21 (s, 3H); MS (ESI): m/e 391.1 (C22H22N4O3+H)+.

Workup

  1. customThe precipitate that formed
  2. washwas washed with ethyl acetate
  3. customdried (14 mg, 6%)

Sources & evidence

ORD record
ord-437b13a90f54440e91d74201485dd335
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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