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

HRID 340828Notes

Reaction equation

HRID 340828 reaction equation
[C:1]([N:4]1[CH2:10][C:9]2[CH:11]=[C:12](/[CH:15]=[CH:16]/[C:17]([N:19]([CH3:31])[CH2:20][C:21]3[O:22][C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]=3[CH3:26])=[O:18])[CH:13]=[N:14][C:8]=2[NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[ClH:32]>C(Cl)Cl.CCOCC>[ClH:32].[C:1]([N:4]1[CH2:10][C:9]2[CH:11]=[C:12](/[CH:15]=[CH:16]/[C:17]([N:19]([CH3:31])[CH2:20][C:21]3[O:22][C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]=3[CH3:26])=[O:18])[CH:13]=[N:14][C:8]=2[NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24891457(E)-3-(4-Acetyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide

Product 1

HCID 24891456(E)-3-(4-Acetyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-3-(4-acetyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (89 mg, 0.21 mmol) in CH2Cl2 (4 mL) was treated with anhydrous HCl (0.21 mL of a 1.0 M solution in Et2O, 0.21 mmol). After stirring for 15 min, the mixture was diluted with Et2O (25 mL) and allowed to stir for 2 h. The solid was isolated by filtration, washed with Et2O and dried under vacuum at 50° C. for 3 days to give the title compound (83 mg, 88%) as a white powder and as a mixture of amide rotamers; 1H NMR (300 MHz, DMSO-d6) δ8.46-8.23 (m, 3H), 7.58-7.22 (m, 6H), 5.02-4.80 (m, 4H), 3.87-3.74 (m, 4H), 3.19-2.90 (m, 3H), 2.26 (s, 3H), 2.03-1.99 (m, 3H); MS (ESI) m/e 419 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-15c377f5c9ee408fb8eda665444a0fc8
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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