Hydrochloric Acid → HCID 16661736, compound

HRID 2097071Notes

Reaction equation

HRID 2097071 reaction equation
[CH3:1][C:2]1([CH3:31])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:30])[CH2:19][C:20]3[O:21][C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[C:24]=3[CH3:25])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1.[ClH:32]>C(Cl)Cl.CCOCC>[ClH:32].[CH3:1][C:2]1([CH3:31])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:30])[CH2:19][C:20]3[O:21][C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[C:24]=3[CH3:25])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10432164HCID 10432164, compound

Product 1

HCID 16661736HCID 16661736, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 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-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.20 g, 0.48 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl (0.48 mL of a 1.0 M solution in Et2O, 0.48 mmol). After stirring for 45 min, the mixture was diluted with Et2O (50 mL) and stirred 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 (0.21 g, 97%) as a white powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.92 (s, 1H), 10.55 (br s, 2H), 8.68-8.65 (m, 1H), 8.39 (s, 1H), 7.60-7.22 (m, 6H), 5.01-4.81 (m, 2H), 4.40 (s, 2H), 3.20-2.93 (m, 3H), 2.27 (s, 3H), 1.63 (s, 6H); MS (ESI) m/e 419 (M+H)+.

Workup

  1. stirringstirred 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-a0d0ece9c00d449fa5e1f370083f6e48
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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