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

HRID 1362294
Notes
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Reaction equation

HRID 1362294 reaction equation
[CH:1]([C:4]1[C:5]([O:31][CH2:32][CH2:33][CH3:34])=[C:6]([CH:28]=[CH:29][CH:30]=1)[CH2:7][N:8]([CH3:27])[C:9](=[O:26])/[CH:10]=[CH:11]/[C:12]1[CH:25]=[N:24][C:15]2[NH:16][C:17](=[O:23])[C:18](C)(C)[NH:19][CH2:20][C:14]=2[CH:13]=1)([CH3:3])[CH3:2].[ClH:35]>C(Cl)Cl.C(OCC)C>[ClH:35].[CH:1]([C:4]1[C:5]([O:31][CH2:32][CH2:33][CH3:34])=[C:6]([CH:28]=[CH:29][CH:30]=1)[CH2:7][N:8]([CH3:27])[C:9](=[O:26])/[CH:10]=[CH:11]/[C:12]1[CH:25]=[N:24][C:15]2[NH:16][C:17](=[O:23])[CH2:18][NH:19][CH2:20][C:14]=2[CH:13]=1)([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 66967492(E)-N-(3-Isopropyl-2-propoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochlorideYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (E)-N-(3-isopropyl-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 (0.158 g, 0.362 mmol) in CH2Cl2 (4 mL) under N2 was treated with anhydrous HCl (0.18 mL of a 2.0 M solution in diethyl ether, 0.36 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 (0.15 g, 91%) as an off white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 11.10-11.07 (m, 1H), 10.07 (br s, 2H), 8.77-8.72 (m, 1H), 8.33-8.24 (m, 1H), 7.63-7.55 (m, 1H), 7.40-7.31 (m, 1H), 7.26-7.21 (m, 1H), 7.13-7.05 (m, 1H), 6.90-6.83 (m, 1H), 4.83-4.67 (m, 2H), 4.28-4.22 (m, 2H), 3.85-3.69 (m, 4H), 3.30-3.25 (m, 1H), 3.14-2.89 (m, 3H), 1.81-1.75 (m, 2H), 1.20-1.17 (m, 6H), 1.06-1.01 (m, 3H); MS (ESI) m/e 437 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-10b8827e5d364d0d9ebbd85032d9bca4
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879872B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes