Ethylenediamine → HCID 71253674, compound

HRID 1774993Notes

Reaction equation

HRID 1774993 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH2:29]([NH2:32])[CH2:30][NH2:31]>>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:31][CH2:30][CH2:29][NH2:32])[CH:7]=4)=[N:9][NH:10][C:11]3=[CH:12][N:13]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 71253405HCID 71253405, compound

Product 1

HCID 71253674HCID 71253674, compoundYield 64%

Procedure

Following the procedure of Example 143, 3-(2-fluoropyridin-4-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and 1,2-ethylenediamine were reacted and purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 32 mg (64%) of 159. ESI MS m/z 332.1 (M+1). 1H NMR (400 MHz, DMSO): 9.38 (s, 1H), 9.23 (s, 1H), 8.60 (d, J=11.0 Hz, 2H), 8.53 (d, J=7.1 Hz, 1H), 8.10 (s, 1H), 7.54 (s, 1H), 7.25 (d, J=11.9 Hz, 2H), 6.67 (s, 1H), 2.78 (s, 2H)

Workup

  1. customwere reacted
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-0fc00daec00441bba385af32cf197c3c
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…