Acetyl chloride → HCID 86713664, compound

HRID 1430521Notes

Reaction equation

HRID 1430521 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]3[C:16]([F:32])=[CH:17][C:18]([F:31])=[C:19]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[CH:20]=3)[C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1.[C:33](Cl)(=[O:35])[CH3:34].C1C[O:40][CH2:39][CH2:38]1>>[C:33]([N:1]([C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]3[CH:20]=[C:19]([NH:21][C:22]([NH:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:23])[C:18]([F:31])=[CH:17][C:16]=3[F:32])[C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1)[C:39](=[O:40])[CH3:38])(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 86713662HCID 86713662, compound

Product 1

HCID 86713664HCID 86713664, compoundYield 84%

Procedure

A solution of 1-(5-(7-amino-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)-3-phenylurea (150 mg, 0.344 mmol) and TEA (174.2 mg, 1.72 mmol) in THF (3 mL) was treated drop-wise with acetyl chloride (81 mg, 1.03 mmol) at RT. The resulting mixture was stirred for 2 h and the solvent was removed to give the crude product. It was diluted, washed with brine, dried over Na2SO4, concentrated under reduced pressure and purified by silica gel chromatography to give N-acetyl-N-{3-[2,4-difluoro-5-(3-phenyl-ureido)-phenyl]-1-ethyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-7-yl}-acetamide (150 mg, 84% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.86 (s, 1H), 9.41 (s, 1H), 8.79 (s, 1H), 8.74 (s, 1H), 8.27 (s, 1H), 8.20-8.16 (m, 1H), 8.08 (s, 1H), 8.00 (s, 1H), 7.46-7.39 (m, 3H), 7.29-7.25 (m, 2H), 6.98-6.95 (m, 1H), 4.25-4.22 (t, J=7.2 Hz, 3H), 2.16 (s, 3H), 1.27 (s, 3H).

Workup

  1. customthe solvent was removed
  2. customto give the crude product
  3. additionIt was diluted
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-efcec68e033a478381465d09c1cf1012
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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