Hydrochloric Acid → HCID 16659979, compound

HRID 1362319Notes

Reaction equation

HRID 1362319 reaction equation
[CH3:1][C:2]1([CH3:33])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:32])[CH2:19][C:20]3[O:21][C:22]4[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=4[C:24]=3[CH2:25][CH2:26][CH3:27])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1.[ClH:34]>C(Cl)Cl.CCOCC>[ClH:34].[CH3:33][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]([CH3:32])[CH2:19][C:20]3[O:21][C:22]4[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=4[C:24]=3[CH2:25][CH2:26][CH3:27])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659980HCID 16659980, compound

Product 1

HCID 16659979HCID 16659979, compoundYield 72%

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-propyl-benzofuran-2-ylmethyl)acrylamide (84.0 mg, 0.188 mmol) in CH2Cl2 (3 mL) was treated with anhydrous HCl (0.094 mL of a 2 M solution in Et2O, 0.188 mmol). After stirring for 1 h, the mixture was diluted with Et2O (5 mL) and then stirred for 10 min. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. overnight to give the title compound (65.0 mg, 72%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.9 (s, 1H), 10.3 (br s, 2H) 8.71-8.65 (m, 1H), 8.37 (s, 1H), 7.60-7.48 (m, 3H), 7.34-7.20 (m, 3H), 5.01-4.81 (m, 2H), 4.41 (s, 2H), 3.20-2.90 (m, 3H), 2.73 (t, J=7.2 Hz, 2H), 1.70-1.61 (m, 8H), 0.93 (t, J=7.5 Hz, 3H); ESI MS m/z 447 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-11e37d65f2184f18a7003411c3662790
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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