Hydrochloric Acid → (E)-3-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrogen chloride

HRID 2097088Notes

Reaction equation

HRID 2097088 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[C:13]([N:15]([CH3:27])[CH2:16][C:17]3[O:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]=3[CH3:22])=[O:14])=[CH:10][C:2]1=2.[ClH:28]>C(Cl)Cl.C(OCC)C>[ClH:28].[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[C:13]([N:15]([CH3:27])[CH2:16][C:17]3[O:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]=3[CH3:22])=[O:14])=[CH:10][C:2]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16660142(E)-3-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide

Product 1

HCID 16660141(E)-3-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrogen chlorideYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (E)-3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.121 g, 0.332 mmol) in CH2Cl2 (4 mL) under N2 was treated with anhydrous HCl (0.16 mL of a 2 M solution in diethyl ether, 0.33 mmol). After stirring for 72 h, the resulting solids were collected by filtration, washed with Et2O (50 mL) and dried to yield the title compound (0.094 g, 71%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 8.74 (br s, 1H), 7.97-7.93 (m, 2H), 7.57-7.55 (m, 1H), 7.49-7.77 (m, 2H), 7.30-7.13 (m, 3H), 4.99-4.77 (m, 2H), 4.25 (br s, 2H), 3.57 (m, 2H), 3.16-2.91 (m, 3H), 2.25 (s, 3H); MS (ESI) m/e 364 (M+H)+.

Workup

  1. filtrationthe resulting solids were collected by filtration
  2. washwashed with Et2O (50 mL)
  3. customdried

Sources & evidence

ORD record
ord-9ad18b3642d143a0965c606a5b6fef06
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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