HCID 25113700, compound → HCID 25113699, compound

HRID 1182983Notes

Reaction equation

HRID 1182983 reaction equation
[Cl:1][C:2]1[C:11]2[C:10]([S:12]([N:15]3[CH2:19][CH2:18][C@H:17]([NH:20][CH3:21])[CH2:16]3)(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[N:4][CH:3]=1>CC(O)C>[ClH:1].[Cl:1][C:2]1[C:11]2[C:10]([S:12]([N:15]3[CH2:19][CH2:18][C@H:17]([NH:20][CH3:21])[CH2:16]3)(=[O:13])=[O:14])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 25113700HCID 25113700, compound

Product 1

HCID 25113699HCID 25113699, compoundYield 182.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
61.5 °C

Procedure

(S)-1-(4-Chloro-5-isoquinolinesulfonyl)-3-(methylamino)pyrrolidine (150 g) obtained in Example 1 was suspended in 2-propanol (2400 ml), and the suspension was warmed to 61.5° C. to dissolve the compound. This solution was filtered by using a membrane filter (internal diameter: 90 mm, ADVANTEC PTFE, 0.2 μm), and the filtrate was added dropwise with 300 ml of a mixed solution of hydrochloric acid (35%, specific gravity: 1.18, 48.0 g, Kanamori Industry) and purified water (261.4 ml, Fukuju Pharmaceuticals) with maintaining the filtrate at 55° C. The mixture was stirred at 55° C. for 44 minutes, then cooled to 2.0° C. over 2 hours and 11 minutes, and further stirred for 1 hour and 28 minutes, and then the deposited crystals were separated by suction filtration using a Buchner funnel (internal diameter: 150 mm, filter paper: No. 5C). The pale brown wet crystals obtained were dried under reduced pressure at 50° C. for 14 hours and 35 minutes to obtain the title compound (152 g).

Workup

  1. dissolutionto dissolve the compound
  2. filtrationThis solution was filtered
  3. filtrationfilter (internal diameter: 90 mm, ADVANTEC PTFE, 0.2 μm)
  4. additionthe filtrate was added dropwise with 300 ml of a mixed solution of hydrochloric acid (35%, specific gravity: 1.18, 48.0 g, Kanamori Industry)
  5. custompurified water (261.4 ml, Fukuju Pharmaceuticals)
  6. temperaturewith maintaining the filtrate at 55° C
  7. temperaturecooled to 2.0° C. over 2 hours and 11 minutes
  8. stirringfurther stirred for 1 hour and 28 minutes
  9. customthe deposited crystals were separated by suction filtration
  10. filtration150 mm, filter paper
  11. customThe pale brown wet crystals obtained
  12. customwere dried under reduced pressure at 50° C. for 14 hours and 35 minutes

Sources & evidence

ORD record
ord-f5d19588f1ce403583c5460365c02f2a
Source dataset
uspto-grants-2014_03
Patent number
US08664243B2

Reaction notes

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