Hydrochloric Acid → HCID 118035228, compound

HRID 1773328Notes

Reaction equation

HRID 1773328 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:26]5[CH2:31][CH2:30][CH2:29][C@@H:28]([NH2:32])[CH2:27]5)=[N:16][C:15]=4[N:14]([CH3:33])[C:12]3=[O:13])=[N:7][C:6]=2[CH:34]=1.[ClH:35]>ClCCl>[ClH:35].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:20](=[O:21])[C:19]4[N:18]([CH2:22][C:23]#[C:24][CH3:25])[C:17]([N:26]5[CH2:31][CH2:30][CH2:29][C@@H:28]([NH2:32])[CH2:27]5)=[N:16][C:15]=4[N:14]([CH3:33])[C:12]3=[O:13])=[N:7][C:6]=2[CH:34]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72703825HCID 72703825, compound

Product 1

HCID 118035228HCID 118035228, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound 1-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-amino-piperidin-1-yl]-xanthine 1 (60 mg, 0.124 mmol) was dissolved in dichloromethane (2 ml). A dichloromethane solution (1 mol/L) of 0.14 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-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-amino-piperidin-1-yl]-xanthine hydrochloride 4 (47 mg, yellow solid), yield: 76%.

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-c72354b8bb6b433282131312aa578cd6
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

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