Triethylamine → HCID 178427844, compound

HRID 2357288Notes

Reaction equation

HRID 2357288 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].Cl.[NH2:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([OH:40])[CH2:36][CH2:35]1.C(N(CC)CC)C>C1COCC1>[OH:40][C@H:37]1[CH2:38][CH2:39][C@H:34]([NH:33][C:16]2[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]3[CH:12]=[CH:11][C:10](=[O:31])[N:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[C:14]=3[N:15]=2)[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 178479278HCID 178479278, compound

Product 1

HCID 178427844HCID 178427844, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 48 (300 mg, 0.67 mmol), trans-4-aminocyclohexanol hydrochloride (226 mg, 1.5 mmol), and triethylamine (0.42 mL, 3 mmol) were combined in THF (15 mL) and stirred under Ar at 500 for 2 days. The solvents were removed in vacuo, and the residue was partitioned between EtOAc and H2O. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography with 0-20% EtOAc/CH2Cl2 followed by recrystallization from CH2Cl2/hexane gave the product as a white-crystalline solid. mp 158-160°, LC MS m/z=481 (MH+). Retention time=2.08 min.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over anhyd Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customFlash chromatography with 0-20% EtOAc/CH2Cl2 followed by recrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-f16535d7b6034ae9b8e311d7e9c58ef0
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

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