Acetic Anhydride → HCID 71585049, compound

HRID 1430509Notes

Reaction equation

HRID 1430509 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]3[C:16]([Br: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](OC(=O)C)(=[O:35])[CH3:34]>>[C:33]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]3[C:16]([Br:32])=[CH:17][C:18]([F:31])=[C:19]([NH:21][C:22]([NH:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:23])[CH:20]=3)[C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1)(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 71585077HCID 71585077, compound

Product 1

HCID 71585049HCID 71585049, compoundYield 57.5%

Conditions

Temperature
110 °C

Procedure

1-(5-(7-amino-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-bromo-2-fluorophenyl)-3-phenylurea (90 mg, 0.181 mmol) was suspended in acetic anhydride (5 mL, 52.9 mmol) and heated at 110° C. for 4 h. The reaction was cooled to RT, poured onto ice (15 g), and stirred overnight. The solids were collected, rinsed well with H2O, air dried, then suspended in MeCN (2-3 mL) and heated at 80° C. overnight. The solids were collected by filtration, rinsed with MeCN and dried under vacuum to afford 1-(5-(7-acetamido-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-bromo-2-fluorophenyl)-3-phenylurea (56 mg, 57% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.84 (s, 1H), 9.10 (s, 1H), 8.73 (d, J=2.4 Hz, 1H), 8.71 (s, 1H), 8.26 (s, 1H), 8.22 (d, J=8.4 Hz, 1H), 7.95 (s, 1H), 7.7 (d, J=6.8 Hz, 1H), 7.42-7.40 (m, 2H), 7.28-7.24 (m, 2H), 6.98-6.95 (m, 1H), 4.19 (q, J=6.8 Hz, 2H), 2.15 (s, 3H), 1.25 (t, J=6.8 Hz, 3H); MS (ESI) m/z: 538.1 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to RT
  2. additionpoured onto ice (15 g)
  3. customThe solids were collected
  4. washrinsed well with H2O, air
  5. customdried
  6. temperatureheated at 80° C. overnight
  7. filtrationThe solids were collected by filtration
  8. washrinsed with MeCN
  9. customdried under vacuum

Sources & evidence

ORD record
ord-13d40e749b15419b8b7303a1d7650f7b
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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