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

HRID 2097069Notes

Reaction equation

HRID 2097069 reaction equation
[CH3:1][C:2]1([CH3:32])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH2:20][C:21]3[O:22][C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[C:25]=3[CH2:26][CH3:27])[CH3:19])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1.[ClH:33]>C(Cl)Cl.CO.CCOCC>[ClH:33].[CH3:32][C:2]1([CH3:1])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH2:20][C:21]3[O:22][C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[C:25]=3[CH2:26][CH3:27])[CH3:19])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 16659982HCID 16659982, compound

Product 1

HCID 16659981(E)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methylacrylamide hydrochlorideYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methylacrylamide (59.0 mg, 0.136 mmol) in CH2Cl2 (4 mL) and CH3OH (0.3 mL) was treated with anhydrous HCl (0.068 mL of a 2 M solution in Et2O, 0.136 mmol). After stirring for 1 h, the mixture was diluted with Et2O (5 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 (63.0 mg, 99%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 10.9 (s, 1H), 10.5 (br s, 2H) 8.71-8.60 (m, 1H), 8.39 (d, J=8.0 Hz, 1H), 7.65-7.50 (m, 3H), 7.35-7.20 (m, 3H), 4.80-5.01 (m, 2H), 4.40 (s, 2H), 3.20-2.90 (m, 3H), 2.77 (d, J=7.0 Hz, 2H), 1.62 (s, 6H), 1.22 (t, J=7.0 Hz, 3H); ESI MS m/z 433 (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-64d387e26edf4918852aea71a17dff17
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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