Hydrochloric Acid → (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-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide hydrochloride

HRID 1362161Notes

Reaction equation

HRID 1362161 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[S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[C:21]=3[CH3:29])=[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[S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[C:21]=3[CH3:29])=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10096283HCID 10096283, compound

Product 1

HCID 10096282(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-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide hydrochlorideYield 96%

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-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide (0.15 g, 0.35 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl in Et2O (0.35 mL, 1.0 M). After stirring for 5 min, the mixture was diluted with Et2O (50 mL) and allowed to stir for 1 h. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 60° C. for 4 d to give the title compound (0.16 g, 96%) as a light yellow powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.92 (s, 1H), 10.56 (br s, 2H), 8.66-8.67 (m, 1H), 8.40 (s, 1H), 7.86-7.89 (m, 1H), 7.73-7.75 (m, 1H), 7.58-7.63 (m, 1H), 7.30-7.40 (m, 3H), 4.90-5.13 (m, 2H), 4.39-4.41 (m, 2H), 2.94-3.17 (m, 3H), 2.43 (s, 3H), 1.63 (s, 6H); MS (ESI) m/e 435 (M+H)+.

Workup

  1. stirringto stir for 1 h
  2. customThe solid was isolated by filtration
  3. washwashed with Et2O
  4. customdried under vacuum at 60° C. for 4 d

Sources & evidence

ORD record
ord-6fb6cb34a76e44c1bfeae91529ba27ff
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…