Ammonia → HCID 66892925, compound

HRID 2250111Notes

Reaction equation

HRID 2250111 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].C([N:34](CC)CC)C.N>CN1C(=O)CCC1.CCOC(C)=O>[NH2:34][C:16]1[N:17]=[C:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[CH3:26])[C:13]2[CH:12]=[CH:11][C:10](=[O:31])[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[C:14]=2[N:15]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8471TriethylamineHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 66892925HCID 66892925, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of the product of Example 48 (1.0 g, 2.2 mmol) and triethylamine (1 mL) in 2 mL of NMP was bubbled NH3 gas at 23° for 30 min. The mixture was diluted with EtOAc and washed with H2O to give the crude material. Purification by flash chromatography eluting with EtOAc/hexane/triethylamine (50/50/2, v/v/v), followed by recrystallization from dichloromethane and hexane, gave the title compound, (360 mg, 43%). LC-MS: 383.0 (MH+, m/z), 1.95 (Rt, min).

Workup

  1. washwashed with H2O
  2. customto give the crude material
  3. customPurification by flash chromatography
  4. washeluting with EtOAc/hexane/triethylamine (50/50/2, v/v/v)
  5. customfollowed by recrystallization from dichloromethane and hexane

Sources & evidence

ORD record
ord-3d92a351c7fc4d53b923bdec8197a195
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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