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

HRID 1362292Notes

Reaction equation

HRID 1362292 reaction equation
[CH3:1][C:2]1([CH3:34])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:22]=3[O:30][CH2:31][CH2:32][CH3:33])[CH3:19])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1.[ClH:35]>C(Cl)Cl.C(OCC)C>[ClH:35].[CH3:34][C:2]1([CH3:1])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:22]=3[O:30][CH2:31][CH2:32][CH3:33])[CH3:19])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659657(E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-isopropyl-2-propoxybenzyl)-N-methylacrylamide

Product 1

HCID 16659656(E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-isopropyl-2-propoxybenzyl)-N-methylacrylamide hydrochlorideYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (E)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-isopropyl-2-propoxybenzyl)-N-methylacrylamide (0.164 g, 0.352 mmol) in CH2Cl2 (4 mL) under N2 was treated with anhydrous HCl (0.17 mL of a 2.0 M solution in diethyl ether, 0.34 mmol) After stirring for 18 h, the resulting solid was collected by filtration, washed with Et2O (100 mL) and dried to yield the title compound (0.12 g, 71%) as an off white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.95 (br s, 1H), 10.25 (br s, 2H), 8.67-8.63 (m, 1H), 8.36-8.26 (m, 1H), 7.62-7.54 (m, 1H), 7.39-7.31 (m, 1H), 7.26-7.20 (m, 1H), 7.13-7.05 (m, 1H), 6.90-6.84 (m, 1H), 4.82-4.67 (m, 2H), 4.41-4.36 (m, 2H), 3.77-3.69 (m, 2H), 3.30-3.25 (m, 1H), 3.16-2.89 (m, 3H), 1.82-1.75 (m, 2H), 1.60-1.58 (m, 6H), 1.23-1.13 (m, 6H), 1.06-1.01 (m, 3H); MS (ESI) m/e 465 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-9f4420a1cc954331ac19e2c71063ec21
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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