HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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 2097040
Notes
Print preview

Reaction equation

HRID 2097040 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-f53d4fc159524b2ba5910b12febc28fa
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450307B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes