Cesium carbonate → N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine

HRID 1042812Notes

Reaction equation

HRID 1042812 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:34]1[CH:35]=[CH:36][N:37]=[C:38]2[C:43]=1[N:42]=[CH:41][C:40]([O:44][CH3:45])=[CH:39]2>CN(C=O)C.O>[CH3:45][O:44][C:40]1[CH:39]=[C:38]2[C:43]([C:34]([O:26][C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:12]4[C:13]5[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=5)[C:9]([C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)=[N:10][N:11]=4)=[CH:25][CH:24]=3)=[CH:35][CH:36]=[N:37]2)=[N:42][CH:41]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 594273408-Chloro-3-methoxy-1,5-naphthyridineHCID 1354520264-{[4-(4-Methoxyphenyl)phthalazin-1-yl]amino}phenol

Product 1

HCID 59427326N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 5 mL microwave tube was charged with 4-(4-(4-methoxyphenyl)phthalazin-1-ylamino)phenol and 3 equivalents of cesium carbonate (342 mg, 1.048 mmol) in 1.8 mL of DMF. The mixture was stirred at RT for 10 min. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (88 mg, 0.454 mmol), the vessel was capped and irradiated at 150° C. for 15 min in the microwave, at which time the reaction was determined complete by LC/MS. The mixture was cooled to ambient temperature and diluted with water. The solids were filtered and washed with water. The solids were triturated with methanol, filtered to remove remaining impurities, washed with additional methanol and dried under vacuum to afford N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine as a light orange solid. MS [M+H]=502; Calc'd 501.54 for C30H25N5O3.

Workup

  1. customthe vessel was capped
  2. customirradiated at 150° C. for 15 min in the microwave, at which time the reaction
  3. temperatureThe mixture was cooled to ambient temperature
  4. filtrationThe solids were filtered
  5. washwashed with water
  6. customThe solids were triturated with methanol
  7. filtrationfiltered
  8. customto remove
  9. washwashed with additional methanol
  10. customdried under vacuum

Sources & evidence

ORD record
ord-2079949e5b3c4e718314e056644f35d7
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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