HCID 86677895, compound → HCID 86677894, compound

HRID 1499970Notes

Reaction equation

HRID 1499970 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:12]([C:14]3[CH:21]=[C:20]([Cl:22])[C:17]([C:18]#[N:19])=[C:16]([CH:23]4[CH2:26][N:25]([CH2:27][C@@H:28]([OH:30])[CH3:29])[CH2:24]4)[C:15]=3[O:31][CH3:32])[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12.NC1N=CN=C2N([C@H](C3C=C(Cl)C(C#N)=C(C4CN(C[C@H](O)C)C4)C=3OC)C)N=C(C)C=12.NC1N=CN=C2N([C@@H](C3C=C(Cl)C(C#N)=C(C4CN(C[C@H](O)C)C4)C=3OC)C)N=C(C)C=12>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[CH:21]=[C:20]([Cl:22])[C:17]([C:18]#[N:19])=[C:16]([CH:23]4[CH2:26][N:25]([CH2:27][CH:28]([OH:30])[CH3:29])[CH2:24]4)[C:15]=3[O:31][CH3:32])[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

4

Reactant 3

HCID 86677895HCID 86677895, compoundHCID 86677896HCID 86677896, compoundHCID 89420804HCID 89420804, compound

Product 1

HCID 86677894HCID 86677894, compound

Procedure

Based on the stereochemistry of Example 269, the stereochemistry of each diastereomer is believed to be 4-((R)-1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-6-chloro-2-(1-((S)-2-hydroxypropyl)azetidin-3-yl)-3-methoxybenzonitrile (Example 361), 4-((5)-1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-6-chloro-2-(1-((R)-2-hydroxypropyl)azetidin-3-yl)-3-methoxybenzonitrile (Example 362), and 4-((R)-1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-6-chloro-2-(1-((R)-2-hydroxypropyl)azetidin-3-yl)-3-methoxybenzonitrile (Example 363) (structures shown below)

Sources & evidence

ORD record
ord-73af0935cca8412d873e26333cf74d28
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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