Triethylamine → HCID 67040463, compound

HRID 605401Notes

Reaction equation

HRID 605401 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:25]=[CH:24][C:12]([C:13]([NH:15][C@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])=[O:14])=[CH:11][C:10]=2[NH:26][C:27]2[C:28]3[CH:36]=[CH:35][C:34]([CH:37]([CH3:39])[CH3:38])=[N:33][C:29]=3[N:30]=[CH:31][N:32]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>C1COCC1.C(OCC)(=O)C>[CH:37]([C:34]1[CH:35]=[CH:36][C:28]2[C:27]([NH:26][C:10]3[CH:11]=[C:12]([CH:24]=[CH:25][C:9]=3[S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:48]([CH3:47])(=[O:50])=[O:49])=[CH:3][CH:4]=3)[C:13]([NH:15][C@H:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:17])=[O:14])=[N:32][CH:31]=[N:30][C:29]=2[N:33]=1)([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 67041061HCID 67041061, compound

Product 1

HCID 67040463HCID 67040463, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 385G (50 mg, 0.094 mmol) and triethylamine (0.030 mL, 0.215 mmol) in THF (1.0 mL) at 0° C. under N2 was treated with methanesulfonyl chloride (0.008 mL, 0.103 mmol) added dropwise then reacted at room temperature for 1 hour. The reaction was recooled to 0° C., followed by additional methanesulfonyl chloride (0.004 mL, 0.052 mmol) added dropwise and reaction at room temperature for 0.5 hours. The mixture was diluted with ethyl acetate (20 mL) and the organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient starting with dichloromethane and ending with ethyl acetate (25 mg, 44%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.33 (d, J=6.99 Hz, 6 H) 1.46 (d, J=6.99 Hz, 3 H) 3.03 (s, 3 H) 3.15-3.28 (m, 1 H) 5.04-5.31 (m, 1 H) 7.09 (d, J=8.09 Hz, 2 H) 7.13-7.27 (m, 3 H) 7.26-7.45 (m, 7 H) 7.62 (d, J=8.46 Hz, 1 H) 7.77 (dd, J=8.27, 1.65 Hz, 1 H) 7.95 (s, 1 H) 8.57 (s, 1 H) 8.82 (d, J=8.46 Hz, 2 H) 10.00 (s, 1 H) 10.20 (s, 1 H).

Workup

  1. additionadded dropwise
  2. customthen reacted at room temperature for 1 hour
  3. customwas recooled to 0° C.
  4. additionadded dropwise
  5. customreaction at room temperature for 0.5 hours
  6. washthe organic layer was washed with saturated NaHCO3 and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with a gradient

Sources & evidence

ORD record
ord-1d9df4af1be54cf0bf5c8153d41e07a5
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…