Lithium Hydroxide → (S)-3-((2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)piperidin-1-yl)-3-methoxypropan-2-ol

HRID 74865Notes

Reaction equation

ClC1C=C2C(C3N=C(N[C@H]4CCCN(CC(O)COC)C4)C(F)=CN=3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.[Cl:41][C:42]1[CH:43]=[C:44]2[C:50]([C:51]3[N:56]=[C:55]([NH:57][CH:58]4[CH2:63][CH2:62][CH2:61][CH2:60][N:59]4[CH:64]([O:68][CH3:69])[C@@H:65]([OH:67])[CH3:66])[C:54]([F:70])=[CH:53][N:52]=3)=[CH:49][N:48](S(C3C=CC(C)=CC=3)(=O)=O)[C:45]2=[N:46][CH:47]=1.[Li+].[OH-]>C1COCC1.O>[Cl:41][C:42]1[CH:43]=[C:44]2[C:50]([C:51]3[N:56]=[C:55]([NH:57][CH:58]4[CH2:63][CH2:62][CH2:61][CH2:60][N:59]4[CH:64]([O:68][CH3:69])[C@@H:65]([OH:67])[CH3:66])[C:54]([F:70])=[CH:53][N:52]=3)=[CH:49][NH:48][C:45]2=[N:46][CH:47]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-[(3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]-1-piperidyl]-3-methoxy-propan-2-ol, 1d, (0.15 g, 0.24 mmol) in THF was added 1N LiOH solution. The reaction mixture was heated in a microwave reactor at 120° C. for 5 minutes. The reaction mixture was diluted with water and the aqueous phase was extracted with EtOAc (twice). The combined organic phases were dried (MgSO4), filtered and concentrated under vacuo. The resulting solid was purified by silica gel chromatography (5-20% MeOH: CH2Cl2) to afford the desired product (537) as a white solid.

Workup

extractionthe aqueous phase was extracted with EtOAc (twice)
dry with materialThe combined organic phases were dried (MgSO4)
filtrationfiltered
concentrationconcentrated under vacuo
customThe resulting solid was purified by silica gel chromatography (5-20% MeOH: CH2Cl2)

Sources & evidence

ORD record: ord-20a86cc98f254574a2b28b6175193e54
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829007B2

Reaction notes

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