HCID 58345952, compound → HCID 44180270, compound

HRID 876940Notes

Reaction equation

HRID 876940 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][CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:3]=1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](B2OC(C)(C)C(C)(C)O2)=[N:22]1>>[NH:21]1[C:29]2[C:24](=[C:25]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([NH:12][CH2:13][CH2:14][C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[N:3]=3)[CH:26]=[CH:27][CH:28]=2)[CH:23]=[N:22]1

Participants

3

Reactant 2

HCID 58345952HCID 58345952, compoundHCID 178431105HCID 178431105, compound

Product 1

HCID 44180270HCID 44180270, compound

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-pyridin-3-yl-ethyl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification by preparative HPLC yielded 144. NMR (CDCl3) 3.08 (t, H, CH2, J=7.06 Hz), 4.01 (m, 2H, CH2), 4.09 (s, 3H, CH3), 5.4 (sbr, H, NH), 7.20 (m, H, ArH), 7.46 (m, H, ArH), 7.55 (m, 2H, 2×ArH), 7.84 (s, H, ArH), 8.35 (d, H, ArH, J=7.21 Hz), 8.45 (m, H, ArH), 8.50 (s, H, ArH), 10.13 (sbr, H, NH). MS: (ESI+) MH+=371.15

Workup

  1. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-b56557c100f9417daf1f9a268c991254
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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