Hydrochloric Acid → HCID 67147455, compound

HRID 1910634Notes

Reaction equation

HRID 1910634 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:29][CH3:30])[C:5]([O:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[CH:12]=[C:13]([N:21]3[CH2:25][CH2:24][C@@H:23]([NH2:26])[CH2:22]3)[CH:14]=[CH:15][C:16]=2[S:17]([CH3:20])(=[O:19])=[O:18])[CH3:9])[CH:7]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([O:29][CH3:30])[C:5]([O:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[CH:12]=[C:13]([N:21]3[CH2:25][CH2:24][C@@H:23]([NH2:26])[CH2:22]3)[CH:14]=[CH:15][C:16]=2[S:17]([CH3:20])(=[O:19])=[O:18])[CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67147358HCID 67147358, compound

Product 1

HCID 67147455HCID 67147455, compoundYield 200%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(3-(1-(5-chloro-2,3-dimethoxyphenyl)ethylamino)-4-(methylsulfonyl)phenyl)pyrrolidin-3-amine (50.0 mg, 0.10 mmol) in dichloromethane (1 mL) was added 0.12 mL (0.12 mmol) of 1 M HCl in diethyl ether. The solution was allowed to stir for 15 minutes and the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and triturated with diethyl ether. The solvent was removed by rotary evaporation to collect the title compound (50.0 mg, 0.10 mmol) in 93% yield. 1H NMR (400 MHz, CD3OD): δ 7.48 (d, 1H), 6.91 (s, 1H), 6.88 (s, 1H), 6.03 (d, 1H), 5.66 (s, 1H), 3.99 (m, 1H), 3.91 (s, 3H), 3.85 (s, 3H), 3.62-3.21 (m, 4), 3.05 (s, 3H), 2.40 (m, 1H), 2.10 (m, 1H), 1.53 (d, 3H); MS (ESI) m/z: 455.1 (M++1).

Workup

  1. customthe solvent was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in dichloromethane
  3. customtriturated with diethyl ether
  4. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-0206813f2b3c414fa8ce02f9752f3896
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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