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

HRID 1362344Notes

Reaction equation

HRID 1362344 reaction equation
[CH2:1]([O:5][C:6]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:7]=1[CH2:8][N:9]([CH3:26])[C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]1[CH:24]=[N:23][C:16]2[NH:17][C:18](=[O:22])[CH2:19][NH:20][CH2:21][C:15]=2[CH:14]=1)[CH:2]([CH3:4])[CH3:3].[ClH:33]>C(Cl)Cl.C(OCC)C>[ClH:33].[CH2:1]([O:5][C:6]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:7]=1[CH2:8][N:9]([CH3:26])[C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]1[CH:24]=[N:23][C:16]2[NH:17][C:18](=[O:22])[CH2:19][NH:20][CH2:21][C:15]=2[CH:14]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16660146HCID 16660146, compound

Product 1

HCID 16660145(E)-N-(2-Isobutoxy-3-methoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochlorideYield 45%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (E)-N-(2-isobutoxy-3-methoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide (0.108 g, 0.246 mmol) in CH2Cl2 (3 mL) under N2 was treated with HCl (0.12 mL of a 2.0 M solution in diethyl ether, 24 mmol). After stirring for 18 h, the resulting solid was collected by filtration and washed with Et2O (100 mL) and dried. The solid was dissolved in CH2Cl2 (2 mL) and layered with hexanes (5 mL). The resulting solids were collected by filtration, washed with Et2O (50 mL) and dried to yield the target compound (0.052 g, 45%) as a tan solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 11.09-11.07 (m, 1H), 10.03 (br s, 2H), 8.77-8.71 (m, 1H), 8.31-8.24 (m, 1H), 7.62-7.54 (m, 1H), 7.38-7.31 (m, 1H), 7.05-6.59 (m, 2H), 6.68-6.59 (m, 1H), 4.81-4.65 (m, 2H), 4.27-4.23 (m, 2H), 3.85-3.82 (m, 2H), 3.79 (s, 3H), 3.72-3.68 (m, 2H), 3.12-2.88 (m, 3H), 2.06-1.97 (m, 1H), 1.00-0.98 (m, 6H); MS (ESI) m/e 439 (M+H)+.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with Et2O (100 mL)
  3. customdried
  4. dissolutionThe solid was dissolved in CH2Cl2 (2 mL)
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed with Et2O (50 mL)
  7. customdried

Sources & evidence

ORD record
ord-6fc5c81430ec4c1290c9a40e9fe9de93
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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