Hydrochloric Acid → HCID 67520828, compound

HRID 1926330Notes

Reaction equation

HRID 1926330 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)=[CH:13][N:12]=1.[ClH:23]>O1CCOCC1>[ClH:23].[ClH:23].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67520829HCID 67520829, compound

Product 1

HCID 67520828HCID 67520828, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-benzofuran-2-yl-5-(1-methyl-1H-pyrazol-4-yl)-pyridin-2-ylamine (60 mg, 0.207 mmol) in dioxane (3 mL) was charged with 4.0 M of HCl in dioxane (1 mL) at rt. Upon addition, a solid precipitated and all solvent was removed in vacuo. MeOH and heptane were added and the solid was filtered off and dried, giving the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=3.89 (s, 3H), 7.31-7.38 (m, 1H), 7.43 (ddd, J=8.3, 7.1, 1.3 Hz, 1H), 7.64 (d, J=0.8 Hz, 1H), 7.71 (dd, J=8.2, 0.6 Hz, 1H), 7.77 (dd, J=7.8, 0.5 Hz, 1H), 8.02 (d, J=0.5 Hz, 1H), 8.32 (s, 1H), 8.42 (d, J=2.0 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H). MS (ES+): m/z=291.07 (100) [MH+]. HPLC: tR=2.67 min (ZQ3, polar—5 min).

Workup

  1. additionUpon addition
  2. customa solid precipitated
  3. customall solvent was removed in vacuo
  4. additionMeOH and heptane were added
  5. filtrationthe solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-30db23a68487406b92f5598e00bb7aec
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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