MLN4924 hydrochloride → Pevonedistat

HRID 715634Notes

Reaction equation

HRID 715634 reaction equation
Cl.[S:2](=[O:32])(=[O:31])([O:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9]([N:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][C@@H:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH2:22]4)[C:14]=3[CH:13]=[CH:12]2)[CH2:8][C@@H:7]1[OH:30])[NH2:3]>C1COCC1>[S:2](=[O:32])(=[O:31])([O:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9]([N:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][C@@H:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH2:22]4)[C:14]=3[CH:13]=[CH:12]2)[CH2:8][C@@H:7]1[OH:30])[NH2:3]

Participants

3

Reactant 1

HCID 66576990MLN4924 hydrochloride

Product 1

HCID 16720766Pevonedistat

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3 volumes of THF were added to amorphous ((1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl sulfamate hydrochloride (192 mg) in a 4 mL vial. The resulting slurry was stirred at RT overnight. An additional 3 volumes of THF were added and the slurry was then kept in the freezer at −20° C. The slurry was filtered and the resulting crystalline material was analyzed without further drying. XRPD data for Form 5 is shown in FIG. 12 and Table 6; DSC and TGA data are both shown in FIG. 13.

Workup

  1. customwas then kept in the freezer at −20° C
  2. filtrationThe slurry was filtered

Sources & evidence

ORD record
ord-7ed9d7c5c75e48c9a874fa69553928a6
Source dataset
uspto-grants-2015_11
Patent number
US09187482B2

Reaction notes

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