Trifluoroacetic acid → HCID 54670786, compound

HRID 1522629Notes

Reaction equation

HRID 1522629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([NH:15][C:16]2[C:17]3[C:18](=[CH:22][N:23](CC4C=CC(OC)=CC=4)[N:24]=3)[N:19]=[CH:20][CH:21]=2)[C:12]([CH3:34])=[CH:11][N:10]=1.FC1C=CC(F)=CC=1C1N=C(NC2C=CN=C3C=NN(CC4C=CC(OC)=CC=4)C=23)C(C)=CN=1.FC(F)(F)C(O)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][NH:24][C:17]=23)[C:12]([CH3:34])=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67469564HCID 67469564, compoundHCID 67470421HCID 67470421, compound

Product 1

HCID 54670786HCID 54670786, compound

Conditions

Temperature
70 °C

Procedure

N-(2-(2,5-Difluorophenyl)-5-methylpyrimidin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(2,5-difluorophenyl)-5-methylpyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and trifluoroacetic acid (48.0 mL) were combined and heated at 70° C. for 3 hours. The reaction mixture was then concentrated to dryness, suspended in DCM (50 mL) and then poured into a stirred saturated solution of sodium bicarbonate (50 mL). The mixture was sonicated and the solids were filtered and dried under vacuum. The dried solid was subsequently washed with EtOAc and dried under vacuum to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.54 (s, 3H) 7.39 (t, J=6.32 Hz, 2H) 7.70 (br. s., 1H) 8.16 (br. s., 1H) 8.41 (br. s., 1H) 8.64 (d, J=5.31 Hz, 1H) 8.71 (s, 1H) 10.24 (br. s., 1H) 14.48 (br. s., 1H). MS [M+H] found, 339.3.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. additionpoured into a stirred saturated solution of sodium bicarbonate (50 mL)
  3. customThe mixture was sonicated
  4. filtrationthe solids were filtered
  5. customdried under vacuum
  6. washThe dried solid was subsequently washed with EtOAc
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7cee02e00bcc4a13b005c2aaa75a1f15
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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