3-Pyridinol,6-chloro-2-methyl-(9CI) → HCID 57964983, compound

HRID 1931702Notes

Reaction equation

HRID 1931702 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[N:30]=[C:29]([CH3:31])[C:28]([OH:32])=[CH:27][CH:26]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:32][C:28]4[C:29]([CH3:31])=[N:30][C:25]([Cl:24])=[CH:26][CH:27]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 450796993-Pyridinol,6-chloro-2-methyl-(9CI)2×HCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57964983HCID 57964983, compoundYield 19%

Procedure

4-[4-(6-Chloro-2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared in 19% yield as a white powder using Method A described for the preparation of Example 92 by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol) with 6-chloro-2-methyl-pyridin-3-ol (Intermediate 3; 28 mg, 0.19 mmol). 1H NMR (300 MHz, CDCl3) δ 1.50 (s, 9H), 1.96-2.06 (m, 2H), 2.20-2.35 (m, 2H), 2.42 (s, 3H), 2.92-3.05 (m, 2H), 4.26-4.38 (m, 2H), 4.90-5.02 (m, 1H), 7.27-7.30 (m, 1H), 7.48 (d, 1H, J=8.4 Hz), 8.15 (s, 1H), 8.47 (s, 1H). Mass spectrum (ES) MH+=445. HRMS Calcd. for C21H26ClN6O3 (MH+): 445.1750. Found: 445.1750.

Sources & evidence

ORD record
ord-8947b12dfe1544bea8af2c73af9b972a
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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