Hydrochloric Acid → HCID 118035615, compound

HRID 1773329Notes

Reaction equation

HRID 1773329 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:20](=[O:21])[C:19]2[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:26]3[CH2:31][CH2:30][CH2:29][C@@H:28]([NH2:32])[CH2:27]3)=[N:16][C:15]=2[N:14]([CH3:33])[C:12]1=[O:13].[ClH:34]>ClCCl>[ClH:34].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:20](=[O:21])[C:19]2[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:26]3[CH2:31][CH2:30][CH2:29][C@@H:28]([NH2:32])[CH2:27]3)=[N:16][C:15]=2[N:14]([CH3:33])[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72703824HCID 72703824, compound

Product 1

HCID 118035615HCID 118035615, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-amino-piperidin-1-yl]-xanthine 2 (100 mg, 0.216 mmol) was dissolved in dichloromethane (3 ml). A dichloromethane solution (1 mol/L) of 0.24 ml hydrogen chloride was added to obtain a reaction mixture. The reaction mixture was stirred for 10 minutes, and the solvent was distilled off. The residue was washed with ethyl acetate, and dried, to obtain the target compound 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-amino-piperidin-1-yl]-xanthine hydrochloride 5 (85 mg, yellow solid), yield: 79%.

Workup

  1. customto obtain a reaction mixture
  2. distillationthe solvent was distilled off
  3. washThe residue was washed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-3d95469314d04d83a0b4b6e22f285024
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

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