Hydrochloric Acid → N-[(3S,5S)-5-(Hydroxymethyl)pyrrolidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamide

HRID 602468Notes

Reaction equation

HRID 602468 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH:20]([CH3:22])[CH3:21])[N:12]=2)=[O:10])[CH2:5][N:4]1C(OC(C)(C)C)=O.Cl>CO>[OH:1][CH2:2][C@H:3]1[NH:4][CH2:5][C@@H:6]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH:20]([CH3:22])[CH3:21])[N:12]=2)=[O:10])[CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67270520tert-Butyl (2S,4S)-2-(hydroxymethyl)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1-carboxylate

Product 1

HCID 59829647N-[(3S,5S)-5-(Hydroxymethyl)pyrrolidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of tert-butyl (2S,4S)-2-(hydroxymethyl)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1-carboxylate (115 mg, 0.286 mmol, step 2 of Example 7) and 10% hydrochloric acid in methanol (5 mL) was stirred at room temperature for 14 h and concentrated under reduced pressure. The resulting residue was basified with saturated sodium hydrogencarbonate aqueous solution, extracted with dichloromethane (100 mL). The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystallized from isopropyl ether to give 79 mg (91%) of the title compound as a white crystal.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with dichloromethane (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-1570b49027a74587bb05746d6b7c6657
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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