Hydrochloric Acid → HCID 16662044, compound

HRID 1362261Notes

Reaction equation

HRID 1362261 reaction equation
[CH3:1][C:2]1([CH3:35])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:34])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[C:21]=3[O:31][CH2:32][CH3:33])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1.[ClH:36]>C(Cl)Cl.C(OCC)C>[ClH:36].[CH3:35][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]([CH3:34])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:29])([F:30])[F:28])[C:21]=3[O:31][CH2:32][CH3:33])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16061423HCID 16061423, compound

Product 1

HCID 16662044HCID 16662044, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution 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-(2-ethoxy-3-trifluoromethoxybenzyl)acrylamide (0.172 g, 0.349 mmol) in CH2Cl2 (4 mL) under N2 was treated with anhydrous HCl (0.17 mL of a 2 M solution in diethyl ether, 0.34 mmol). After stirring for 18 h, the resulting solid was collected by filtration, washed with Et2O (100 mL) and dried to yield the title compound (0.11 g, 62%) as an off white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.94 (br s, 1H), 10.38 (br s, 2H), 8.67-8.64 (m, 1H), 8.38-8.30 (m, 1H), 7.62-7.54 (m, 1H), 7.41-7.10 (m, 4H), 4.89-4.70 (m, 2H), 4.41-4.36 (m, 2H), 4.06-4.00 (m, 2H), 3.17-2.87 (m, 3H), 1.61-1.59 (m, 6H), 1.37-1.31 (m, 3H); MS (ESI) m/e 493 (M+H)+.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with Et2O (100 mL)
  3. customdried

Sources & evidence

ORD record
ord-f19d516db5a84c61bf367c910093dca3
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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