Acetic Anhydride → HCID 56592379, compound

HRID 1629918Notes

Reaction equation

HRID 1629918 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[N:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[C:23]3[NH2:28])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[N:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[C:23]3[NH:28][C:29](=[O:31])[CH3:30])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 56591765HCID 56591765, compound

Product 1

HCID 56592379HCID 56592379, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 37 mg (0.10 mmol) 5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-[2,6]naphthyridin-1-ylamine in 0.5 ml acetic acid was treated with 20.4 mg (0.20 mmol) acetic acid anhydride and heated to 80° C. The reaction mixture was stirred at this temperature for 18 hours. The reaction mixture was cooled to room temperature and partitioned between 25% aqueous ammonia and dichloromethane. The organic phase was dried over sodium sulphate and evaporated. The residue was triturated with tert-butyl-methylether yielding N-{5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-[2,6]naphthyridin-1-yl}-acetamide as brown crystals; HPLC/MS (A) 1.64 min, [M+H] 410.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between 25% aqueous ammonia and dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was triturated with tert-butyl-methylether

Sources & evidence

ORD record
ord-64c688b3b6544119a3449f81f3495ad7
Source dataset
uspto-grants-2014_07
Patent number
US08791113B2

Reaction notes

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