Hydrochloric Acid → (E)-N-(3-Chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide hydrochloride

HRID 1362277Notes

Reaction equation

HRID 1362277 reaction equation
[Cl:1][C:2]1[C:3]([O:29][CH2:30][CH2:31][CH3:32])=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]([CH3:25])[C:7](=[O:24])/[CH:8]=[CH:9]/[C:10]1[CH:23]=[N:22][C:13]2[NH:14][C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[NH:17][CH2:18][C:12]=2[CH:11]=1.Cl>C(Cl)Cl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[C:3]([O:29][CH2:30][CH2:31][CH3:32])=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]([CH3:25])[C:7](=[O:24])/[CH:8]=[CH:9]/[C:10]1[CH:23]=[N:22][C:13]2[NH:14][C:15](=[O:21])[C:16]([CH3:19])([CH3:20])[NH:17][CH2:18][C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16662049(E)-N-(3-Chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide

Product 1

HCID 16662048(E)-N-(3-Chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide hydrochlorideYield 154.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (E)-N-(3-chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide (0.300 g, 0.656 mmol) in CH2Cl2 (7 mL) under N2 was treated with anhydrous HCl (0.32 mL of a 2 M solution in diethyl ether, 0.64 mmol) After stirring for 7 h, the resulting solid was collected by filtration, washed with Et2O (100 mL) and then dried to yield the target compound (0.25 g, 79%) as an off white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.93 (br s, 1H), 10.38 (br s, 2H), 8.66-8.63 (m, 1H), 8.37-8.28 (m, 1H), 7.62-7.54 (m, 1H), 7.44-7.32 (m, 2H), 7.19-7.02 (m, 2H), 4.87-4.69 (m, 2H), 4.41-4.37 (m, 2H), 3.94-3.87 (m, 2H), 3.16-2.89 (m, 3H), 1.83-1.76 (m, 2H), 1.61-1.59 (m, 6H), 1.05-0.99 (m, 3H); MS (APCI) m/e 457 (M+H)+.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with Et2O (100 mL)
  3. customdried

Sources & evidence

ORD record
ord-ee3f5932347741d2943160055bf7d99a
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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