HCID 22050178, compound → HCID 22050179, compound

HRID 1832006Notes

Reaction equation

HRID 1832006 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[C:10](=[O:42])[N:11]([CH2:26][C:27]2[CH:32]=[N:31][C:30]([C:33]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[O:34])=[CH:29][N:28]=2)[C:12]([CH3:25])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24]>[OH-].[Na+]>[Br:8][C:9]1[C:10](=[O:42])[N:11]([CH2:26][C:27]2[CH:32]=[N:31][C:30]([C:33]([N:35]3[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)=[O:34])=[CH:29][N:28]=2)[C:12]([CH3:25])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24]

Participants

3

Reactant 1

HCID 22050178HCID 22050178, compound

Product 1

HCID 22050179HCID 22050179, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-Bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-1-({5-[(4-methylpiperazin-1-yl)carbonyl]pyrazin-2-yl}methyl)pyridin-2(1H)-one trifluoroacetate (0.17 g, 0.00026 mol) in 0.1N NaOH (25 mL) was stirred at room temperature for 15 min. and extracted the product in ethyl acetate (2×20 mL). The combined organic extracts were washed with water (2×20 mL), dried (Na2SO4) and concentrated to dryness. The residue was dried in vacuo to afford the title product (0.09 g, 64%) as a white powder: 1H NMR (CD3OD/400 MHz) δ 8.69 (d. 1H, J=1.2 Hz), 8.67 (d, 1H, J=1.2 Hz), 7.60 (m, 1H), 7.00 (m, 2H), 6.54 (s, 1H), 5.50 (s, 2H), 5.30 (s, 2H), 3.78 (t, 2H, J=4.8 Hz), 3.58 (t, 2H, J=4.8 Hz), 2.526 (s, 3H), 2.53 (t, 2H, J=4.8 Hz), 2.44 (t, 2H, J=4.8 Hz), and 2.31 (s, 3H); 19F NMR (CD3OD/400 MHz)=δ−111.65 (m) and −116.06 (m); ES-HRMS m/z 548.1123 (M+H C24H25N5O3BrF2 requires 548.1103).

Workup

  1. extractionextracted the product in ethyl acetate (2×20 mL)
  2. washThe combined organic extracts were washed with water (2×20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-851304f2b76a427da295f8fef429326a
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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