HCID 58345946, compound → HCID 44180500, compound

HRID 876947Notes

Reaction equation

HRID 876947 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][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:3]=1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](B2OC(C)(C)C(C)(C)O2)=[N:20]1>>[NH:19]1[C:27]2[C:22](=[C:23]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([NH:12][CH:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[N:3]=3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[N:20]1

Participants

3

Reactant 2

HCID 58345946HCID 58345946, compoundHCID 178431105HCID 178431105, compound

Product 1

HCID 44180500HCID 44180500, compound

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification on silica yielded 154. NMR (CDCl3) 1.70-1.80 (m, 2H, CH2), 2.24-2.27 (m, 2H, CH2), 3.67-3.73 (m, 2H, CH2), 4.11-4.14 (m, 2H, CH2), 4.18 (s, 3H, CH3), 4.55 (m, H, CH), 5.32 (sbr, H, NH), 7.55 (t, H, ArH, J=7.76 Hz), 7.63 (d, H, ArH, J=8.27 Hz), 7.92 (s, H, ArH), 8.40 (d, H, ArH, J=7.23 Hz), 9.16 (s, H, ArH), 10.22 (sbr, H, NH). MS: (ESI+) MH+=350.16

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-99831ed189b84a68a97fc817e4024944
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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