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

HRID 2097062Notes

Reaction equation

HRID 2097062 reaction equation
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH2:12][N:13]([CH3:30])[C:14](=[O:29])/[CH:15]=[CH:16]/[C:17]1[CH:28]=[N:27][C:20]2[NH:21][C:22](=[O:26])[CH2:23][NH:24][CH2:25][C:19]=2[CH:18]=1)[CH3:2].[ClH:31]>C(Cl)Cl.CO.CCOCC>[ClH:31].[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH2:12][N:13]([CH3:30])[C:14](=[O:29])/[CH:15]=[CH:16]/[C:17]1[CH:28]=[N:27][C:20]2[NH:21][C:22](=[O:26])[CH2:23][NH:24][CH2:25][C:19]=2[CH:18]=1)[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 16659825(E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide

Product 1

HCID 16659824(E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochlorideYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide (100 mg, 0.247 mmol) in CH2Cl2 (3 mL) and CH3OH (0.5 mL) was treated with anhydrous HCl (0.123 mL of a 2M solution in Et2O, 0.247 mmol). After stirring for 1 h, the mixture was diluted with Et2O (3 mL) and stirred for 10 minutes. The solid was isolated by filtration, washed with Et2O and dried under vacuum at 50° C. overnight to give the title compound (81.0 mg, 81%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 10.0 (br s, 2H), 8.82-8.75 (m, 1H), 8.33-8.27 (m, 1H), 7.68-7.55 (m, 3H), 7.50 (t, J=7.5 Hz, 1H), 7.33-7.24 (m, 3H), 5.01-4.81 (m, 2H), 4.26 (s, 2H), 3.84 (s, 2H), 3.20-2.92 (m, 3H), 2.78-2.74 (m, 2H), 1.23-1.19 (m, 3H); ESI MS m/z 405 (M+H)+.

Workup

  1. stirringstirred for 10 minutes
  2. customThe solid was isolated by filtration
  3. washwashed with Et2O
  4. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-3922c621405e412a895390a7ea38aeb3
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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