(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-phenoxy-ethyl)-amine → 6-(1h-Indazol-4-yl)-1-methyl-n-(2-phenoxyethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876938Notes

Reaction equation

HRID 876938 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][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](B2OC(C)(C)C(C)(C)O2)=[N:23]1>>[NH:22]1[C:30]2[C:25](=[C:26]([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][O:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:3]=3)[CH:27]=[CH:28][CH:29]=2)[CH:24]=[N:23]1

Participants

3

Reactant 2

HCID 58345951(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-phenoxy-ethyl)-amineHCID 178431105HCID 178431105, compound

Product 1

HCID 441802696-(1h-Indazol-4-yl)-1-methyl-n-(2-phenoxyethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-phenoxy-ethyl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification by preparative HPLC yielded 143. NMR (CDCl3) 4.19 (s, 3H, CH3), 4.27 (m, 2H, CH2), 4.36 (m, 2H, CH3), 5.83 (sbr, H, NH), 7.00 (m, 3H, 3×ArH), 7.32 (m, 2H, 2×ArH), 7.55 (m, H, ArH), 7.64 (m, H, ArH), 7.96 (s, H, ArH), 8.45 (d, H, ArH, J=7.23 Hz0, 9.18 (s, H, ArH), 10.16 (sbr, H, NH). MS: (ESI+) MEI+=386.19

Workup

  1. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-116d15cdf9da44d0989a086b04774aac
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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