HCID 58345956, compound → HCID 44180610, compound

HRID 876950Notes

Reaction equation

HRID 876950 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=2)[N:3]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](B2OC(C)(C)C(C)(C)O2)=[N:24]1>>[NH:23]1[C:31]2[C:26](=[C:27]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=4)[N:3]=3)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[N:24]1

Participants

3

Reactant 2

HCID 58345956HCID 58345956, compoundHCID 178431105HCID 178431105, compound

Product 1

HCID 44180610HCID 44180610, compound

Procedure

N-[4-(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-phenyl]-acetamide was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification on silica and trituration yielded 157. NMR: (CDCl3): 2.08 (s, 3H, CH3), 4.17 (s, 3H, CH3), 7.51 (t, H, ArH, J=7.77 Hz), 7.69 (m, 3H, 3×ArH), 7.78 (m, 2H, 2×ArH), 8.28 (d, H, ArH, J=7.26 Hz), 8.17 (sbr, H, NH), 8.93 (s, H, ArH), 9.98 (s, H, ArH), 10.07 (s, H, ArH), 13.18 (s, H, ArH). MS: (ESI+) MH+=399.13

Workup

  1. customPurification on silica and trituration

Sources & evidence

ORD record
ord-7365788546db44b9989193d1aad614ae
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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