Hydrochloric Acid → (E)-3-(3,3-Dimethyl-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrochloride

HRID 340823Notes

Reaction equation

HRID 340823 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:8][NH:7][C:6]2[N:9]=[CH:10][C:11](/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:29])[CH2:18][C:19]3[O:20][C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[C:23]=3[CH3:24])=[O:16])=[CH:12][C:5]=2[CH:4]=[N:3]1.[ClH:31]>C(Cl)Cl.CCOCC>[ClH:31].[CH3:1][C:2]1([CH3:30])[CH2:8][NH:7][C:6]2[N:9]=[CH:10][C:11](/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:29])[CH2:18][C:19]3[O:20][C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[C:23]=3[CH3:24])=[O:16])=[CH:12][C:5]=2[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59332851(E)-3-(3,3-Dimethyl-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide

Product 1

HCID 68413288(E)-3-(3,3-Dimethyl-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-3-(3,3-dimethyl-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.11 g, 0.27 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl (0.27 mL of a 1.0 M solution in Et2O, 0.27 mmol). After stirring for 15 min, the mixture was diluted with Et2O (50 mL) and allowed to stir for 3 h. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. overnight to give the title compound (0.10 g, 86%) as a yellow powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ13.16-13.13 (m, 1H), 9.67-9.65 (m, 1H), 8.96-8.92 (m, 1H), 8.69 (s, 1H), 8.64-8.61 (m, 1H), 7.58-7.24 (m, 6H), 5.00-4.80 (m, 2H), 4.54 (br s, 2H), 3.19-2.92 (m, 3H), 2.27 (s, 3H), 1.36 (br s, 6H); MS (ESI) m/e 403 (M+H)+.

Workup

  1. stirringto stir for 3 h
  2. customThe solid was isolated by filtration
  3. washwashed with Et2O
  4. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-dca935d9acbc4fdebe1a7a1e5d513a3c
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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