HCID 58345954, compound → HCID 44180501, compound

HRID 876948Notes

Reaction equation

HRID 876948 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][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]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][N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[N:3]=3)[CH:26]=[CH:27][CH:28]=2)[CH:23]=[N:22]1

Participants

3

Reactant 2

HCID 58345954HCID 58345954, compoundHCID 178431105HCID 178431105, compound

Product 1

HCID 44180501HCID 44180501, compound

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-morpholin-4-yl-ethyl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification on silica yielded 155. NMR (CDCl3) 2.50 (m, 4H, 2×CH2), 2.70 (t, 2H, CH2, J=5.95 Hz), 3.71 (m, 4H, 2×CH2), 3.80 (m, 2H, CH2), 4.08 (s, 3H, CH3), 3.05 (sbr, H, NH), 7.44 (t, H, ArH, J=7.32 Hz), 7.54 (d, H, ArH, J=XXHz), 7.87 (s, H, ArH), 8.35 (m, H, ArH), 9.08 (s, H, NH). MS: (ESI+) MH+=379.17

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-2d1b5319f4414402b2c458c5133b2979
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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