Dimethylformamide → HCID 178505551, compound

HRID 2284613Notes

Reaction equation

HRID 2284613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([C:24](=O)[CH3:25])=[CH:22][N:23]=4)[CH:20]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C[N:28]([CH:30]=O)C.[NH2:32]N>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([C:24]5[CH:25]=[CH:30][NH:28][N:32]=5)=[CH:22][N:23]=4)[CH:20]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9321HydrazineHCID 86715530HCID 86715530, compound

Product 1

HCID 178505551HCID 178505551, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(6-(2-(3-Chloro-4-fluorophenyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)ethan-1-one (300 mg) and DMF.DMA (5 mL) were heated at 95° C. and stirred in a screw capped vial overnight. The reaction mixture was concentrated and the semi-solid residue was diluted with Et2O/hexanes (1:1). The solid was filtered and dried. The enamine (75 mg) and the hydrazine (1.2 eq) were heated in a screw capped vial at 100° C. for 12 h. The reaction mixture was concentrated and purified by preparative HPLC. 1H NMR (300 MHz, DMSO-d6): δ 13.02 (br s), 9.71 (dd, J=1.8, 1.0 Hz, 1H), 8.79 (dd, J=4.8, 1.6 Hz, 1H), 8.62 (s, 1H), 8.06 (dd, J=7.8, 1.7 Hz, 1H), 8.01 (d, J=2.4 Hz, 1H), 7.89 (dd, J=9.3, 0.9 Hz, 1H), 7.74 (dd, J=7.3, 2.1 Hz, 1H), 7.62 (dd, J=7.8, 4.8 Hz, 1H), 7.50 (dd, J=9.3, 1.7 Hz, 1H), 7.37-7.14 (m, 2H), 6.95 (d, J=2.4 Hz, 1H). 19F NMR (282 MHz, DMSO-d6): δ −116.76 (q, J=7.3 Hz). LCMS: rt 4.98 min (A), purity 99%, MS (m/e) 390 MH+.

Workup

  1. customcapped vial overnight
  2. concentrationThe reaction mixture was concentrated
  3. additionthe semi-solid residue was diluted with Et2O/hexanes (1:1)
  4. filtrationThe solid was filtered
  5. customdried
  6. customcapped vial at 100° C. for 12 h
  7. concentrationThe reaction mixture was concentrated
  8. custompurified by preparative HPLC
  9. customrt 4.98 min (A), purity 99%, MS (m/e) 390 MH+

Sources & evidence

ORD record
ord-a8b8f84e4e05462ba3963321fa108d32
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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