(1R,2S,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol → (1S,2S,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

HRID 526972Notes

Reaction equation

HRID 526972 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@@H:20]([OH:24])[C@H:19]4[OH:25])[C:14]([F:26])=[CH:13][N:12]=3)=[CH:9][N:8]([S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:5]2=[N:6][CH:7]=1.ClC1N=C(N[C@H]2CCC[C@H](O)[C@H]2O)C(F)=CN=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C@H:20]([OH:24])[C@H:19]4[OH:25])[C:14]([F:26])=[CH:13][N:12]=3)=[CH:9][N:8]([S:27]([C:30]3[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=3)(=[O:29])=[O:28])[C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 68007372(1R,2S,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diolHCID 86667421(1S,2S,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

Product 1

HCID 68008217(1S,2S,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

Procedure

According to the method for compound 31c, except use compound 32b (0.03 g, 0.11 mmol), to give compound 32c (0.06 g, 0.11 mmol).

Sources & evidence

ORD record
ord-bc4d65ae249b4956ae846ff195cac3c5
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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