Benzyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate → HCID 86677704, compound

HRID 1499773Notes

Reaction equation

HRID 1499773 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:36][CH2:37][CH3:38])=[C:16]([CH:22]4[CH2:25][N:24](C(OCC5C=CC=CC=5)=O)[CH2:23]4)[C:17]([CH3:21])=[C:18]([Cl:20])[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12>[Pd]>[NH:24]1[CH2:23][CH:22]([C:16]2[C:15]([O:36][CH2:37][CH3:38])=[C:14]([CH:12]([N:8]3[C:4]4=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]4[C:10]([CH3:11])=[N:9]3)[CH3:13])[CH:19]=[C:18]([Cl:20])[C:17]=2[CH3:21])[CH2:25]1

Participants

3

Reactant 1

HCID 86677703Benzyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate

Product 1

HCID 86677704HCID 86677704, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Benzyl 3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}azetidine-1-carboxylate (chiral intermediate from first peak of previous step) was hydrogenated in the presence of 5% palladium as described in Example 94, Step 2 to give the desired chiral product. LCMS calculated for C20H26ClN6O (M+H)+: m/z=401.2; Found: 401.1.

Workup

  1. customto give the desired chiral product

Sources & evidence

ORD record
ord-255e2eb07547480b87affe66baa0f9d8
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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