Triethylamine → HCID 178427843, compound

HRID 556620Notes

Reaction equation

HRID 556620 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[C:10]=3[N:11]=[C:12](S(C)(=O)=O)[N:13]=2)=[C:4]([CH3:30])[CH:3]=1.Cl.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]1.C(N(CC)CC)C>C1COCC1>[OH:39][C@H:36]1[CH2:37][CH2:38][C@H:33]([NH:32][C:12]2[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[CH3:30])[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[C:10]=3[N:11]=2)[CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10113314HCID 10113314, compoundHCID 178479278HCID 178479278, compound

Product 1

HCID 178427843HCID 178427843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 59 (200 mg, 0.47 mmol), trans-4-aminocyclohexanol hydrochloride (151 mg, 1 mmol), and triethylamine (0.28 mL, 2 mmol) were combined in THF (10 mL) and stirred under Ar at 50° 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 pale yellow crystalline solid. mp 148-151°, LC MS m/z=463 (MH+) Retention time=2.0 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-51798929c24c4f4e83337885123eb25e
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

Loading…