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

HRID 1362159Notes

Reaction equation

HRID 1362159 reaction equation
[ClH:1].CCOCC.[CH3:7][N:8]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]=1[CH2:37][CH2:38][CH3:39])[C:9](=[O:25])/[CH:10]=[CH:11]/[C:12]1[CH:24]=[N:23][C:15]2[NH:16][C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH2:20][C:14]=2[CH:13]=1>C(Cl)Cl>[ClH:1].[CH3:7][N:8]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]=1[CH2:37][CH2:38][CH3:39])[C:9](=[O:25])/[CH:10]=[CH:11]/[C:12]1[CH:24]=[N:23][C:15]2[NH:16][C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH2:20][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 9956756(E)-N-Methyl-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(1-propyl-naphthalen-2-ylmethyl)acrylamide

Product 1

HCID 9956755(E)-N-Methyl-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(1-propyl-naphthalen-2-ylmethyl)acrylamide hydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 M solution of hydrogen chloride in Et2O (0.25 ml, 0.518 mmol) was added to (E)-N-methyl-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(1-propyl-naphthalen-2-ylmethyl)acrylamide (0.229 g, 0.518 mmol) in CH2Cl2 (5 mL) via syringe. The solution was allowed to stir for 18 h during time which a precipitate fell out of the solution. The product was collected by filtration and was washed with Et2O (100 mL). The product was dried to give the title compound (0.182 g, 73%) as an orange solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 12.00 (br s, 1H), 11.22 (s, 1H), 8.86-8.82 (m, 1H), 8.38-8.32 (m, 1H), 7.94-7.87 (m, 4H), 7.74-7.29 (m, 5H), 6.06-5.64 (m, 1H), 4.40-4.30 (m, 2H), 3.94-3.91 (br s, 2H), 2.93-2.57 (m, 6H), 2.10-2.05 (m, 2H), 1.37-1.32 (m, 2H), 1.02-0.97 (m, 3H); MS (ESI) m/e 443 (M+H)+.

Workup

  1. filtrationThe product was collected by filtration
  2. washwas washed with Et2O (100 mL)
  3. customThe product was dried

Sources & evidence

ORD record
ord-c636a0b8ab524df5873438951f94bf78
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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