Methanesulfonic Acid → HCID 178441804, compound

HRID 705140Notes

Reaction equation

HRID 705140 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([NH2:25])[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].[CH3:26][S:27]([OH:30])(=[O:29])=[O:28]>C(#N)C>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[CH2:1]([C:5]1[N:6]=[C:7]([NH2:25])[C:8]2[NH:13][N:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6395Methanesulfonic Acid2×HCID 178441801HCID 178441801, compound

Product 1

HCID 178441804HCID 178441804, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

5-Butyl-3-(6-(pyrrolidin-1-yl)hexyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (200.3 mg) slurried in acetonitrile (2 mL) at 70° C. was treated with anhydrous methane sulfonic acid (38 ul, 1.0 eq). The resulting reaction mixture turned over to a solution on addition of methane sulfonic acid and on aging at 70° C. started to precipitate solid. The resulting slurry was found to set solid and therefore additional acetonitrile (2 mL) was added to mobilise the slurry. The resulting reaction mixture was allowed to cool to 20° C. and was aged overnight at 20° C. before being filtered and washed with fresh acetonitrile (2×4 mL) to yield a white solid which was oven dried at 40° C. in vacuo (90 mbar) overnight to afford the title compound (234 mg).

Workup

  1. customThe resulting reaction mixture
  2. customon aging at 70° C.
  3. customto precipitate solid
  4. additionadditional acetonitrile (2 mL) was added
  5. customThe resulting reaction mixture
  6. filtrationbefore being filtered
  7. washwashed with fresh acetonitrile (2×4 mL)
  8. customto yield a white solid which
  9. customdried at 40° C. in vacuo (90 mbar) overnight

Sources & evidence

ORD record
ord-aec4677f7fec4e69bf18e9942d7d7dd2
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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