Hydrochloric Acid → HCID 11560746, compound

HRID 2426023Notes

Reaction equation

HRID 2426023 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][C:6]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:4])=[O:3].[ClH:28]>ClCCl.C(OCC)C>[ClH:28].[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[CH:7][C:6]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11560747HCID 11560747, compound

Product 1

HCID 11560746HCID 11560746, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine (120.0 mg, 0.31 mmol) in dichloromethane (2 mL) was added 0.4 mL of 1 M HCl in diethyl ether. The solution was allowed to stir for 1 h, after which a precipitate formed. The solvent was removed by rotary evaporation to collect the title compound (122.0 mg, 0.29 mmol) in 94% yield. 1H NMR (400 MHz, CD3OD): δ 7.94 (d, 1H), 7.91 (d, 1H), 7.84 (d, 1H), 7.73 (d, 1H), 7.50 (m, 4H), 6.60 (d, 1H), 6.29 (s, 1H), 3.47 (m, 4H), 3.21 (m, 4H), 3.19 (s, 3H); MS (ESI) m/z: Calculated for C21H24N3O2S: 382.2; Observed: 382.4 (M++1).

Workup

  1. customafter which a precipitate formed
  2. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-857aaeec78974ab9a42b3741f46d931b
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

Loading…