Hydrochloric Acid → MLN4924 hydrochloride

HRID 715631Notes

Reaction equation

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

Participants

Conditions

Temperature: 22.5 °C

Procedure

To a reaction vessel is added ((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 (1 equiv.) and ethanol (15 volumes with respect to input material) and the mixture is stirred at 20-25° C. 1.0M hydrogen chloride in ethanol (1 equiv. with respect to input material) is added at a rate as to maintain temperature at ≦25° C. The mixture is then stirred at 20±5° C. for a minimum of 4 hours. The solid product is isolated by filtration and washed with ethanol (2×2.5 volumes with respect to input material). The product is then dried by aspiration on the filter and then under reduced pressure at a temperature of 30±5° C. to give the title compound.

Workup

temperatureto maintain temperature at ≦25° C
stirringThe mixture is then stirred at 20±5° C. for a minimum of 4 hours
customThe solid product is isolated by filtration
washwashed with ethanol (2×2.5 volumes with respect to input material)
customThe product is then dried by aspiration on the
filtrationfilter

Sources & evidence

ORD record: ord-f808676ce36a4c099d648f5f3a3bbe76
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187482B2

Reaction notes

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