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

HRID 1362337Notes

Reaction equation

HRID 1362337 reaction equation
[CH3:1][C:2]1([CH3:29])[O:7][C:6]2[CH:8]=[C:9](/[CH:12]=[CH:13]/[C:14]([N:16]([CH3:28])[CH2:17][C:18]3[O:19][C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]=3[CH3:23])=[O:15])[CH:10]=[N:11][C:5]=2[NH:4][CH2:3]1.[ClH:30]>C(Cl)Cl.C(OCC)C>[ClH:30].[CH3:1][C:2]1([CH3:29])[O:7][C:6]2[CH:8]=[C:9](/[CH:12]=[CH:13]/[C:14]([N:16]([CH3:28])[CH2:17][C:18]3[O:19][C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]=3[CH3:23])=[O:15])[CH:10]=[N:11][C:5]=2[NH:4][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659991(E)-3-(2,2-Dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide

Product 1

HCID 16659990(E)-3-(2,2-Dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrogen chlorideYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (E)-3-(2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.147 g, 0.375 mmol) in CH2Cl2 (4 mL) under N2 was treated with anhydrous HCl (0.18 mL of a 2 M solution in diethyl ether, 0.37 mmol). After stirring for 6 h, the resulting solids were collected by filtration, washed with Et2O (50 mL) and dried to yield the title compound (0.14 g, 88%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 8.69 (br s, 1H), 8.00-7.94 (m, 2H), 7.57-7.55 (m, 1H), 7.49-7.44 (m, 2H), 7.30-7.14 (m, 3H), 4.99-4.77 (m, 2H), 3.37 (br s, 2H), 3.15-2.90 (m, 3H), 2.25 (s, 3H), 1.32 (s, 6H); MS (ESI) m/e 392 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-a2e78fbf282f4aad90978f5aef34a710
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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