3-Methoxyaniline → HCID 58345961, compound

HRID 876941Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]2[N:9]([CH2:12][CH3:13])[N:10]=[CH:11][C:3]=12.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1>>[Cl:8][C:6]1[N:5]=[C:4]2[N:9]([CH2:12][CH3:13])[N:10]=[CH:11][C:3]2=[C:2]([NH:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH3:14])[CH:17]=2)[N:7]=1

Participants

Reactant 2

HCID 108243-Methoxyaniline

HCID 583459584,6-Dichloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 58345961HCID 58345961, compound

Procedure

4,6-Dichloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidine 5b was reacted with m-anisidine using General Procedure B to give (6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxy-phenyl)-amine, which was reacted with indazole boronic acid pinacol ester using General Procedure A to give 147. NMR (CDCl3): 1.62 (3H, t), 3.88 (3H, s), 4.62 (2H, q), 6.89 (1H, dd), 7.17 (1H, d), 7.32 (1H, s), 7.40 (1H, t), 7.51 (1H, s), 7.55 (1H, t), 7.64 (1H, d), 8.45 (1H, d), 9.16 (1H, s), 10.20 (1H, br). MS: MH+ 386.19 (100%)

Sources & evidence

ORD record: ord-8fffe4b2ba274002a35979863d737a3d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987280B2

Reaction notes

Loading…