Hydrochloric Acid → HCID 178441803, compound

HRID 705141Notes

Reaction equation

HRID 705141 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].[ClH:26]>C(#N)C.CC(O)C>[ClH:26].[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178441801HCID 178441801, compound

Product 1

HCID 178441803HCID 178441803, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

5-Butyl-3-(6-(pyrrolidin-1-yl)hexyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (197.2 mg) was slurried in acetonitrile (2 mL) at 70° C. before treated with 1.25M HCl in IPA (0.458 mL) which generated a solution. On aging at 70° C. the reaction started to precipitate a solid and this stayed mobile throughout age at 70° C. and therefore the reaciton was cooled to 20° C. The resulting slurry 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. The resulting solid (144 mg) was further dried in vacuo at 50° C. to afford the title compound.

Workup

  1. customOn aging at 70° C.
  2. customto precipitate a solid
  3. filtrationbefore being filtered
  4. washwashed with fresh acetonitrile (2×4 mL)
  5. customto yield a white solid which
  6. customdried at 40° C. in vacuo (90 mbar) overnight
  7. dry with materialThe resulting solid (144 mg) was further dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-732d9d584b694dc2831437cbcde878c7
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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