Ethanol → HCID 68088960, compound

HRID 509549Notes

Reaction equation

HRID 509549 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]3[C:15]([N:32]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])C(=O)OC(C)(C)C)=[N:16][CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][N:21]=4)[CH:19]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1.C(O)C.[CH3:50][NH2:51]>C(Cl)Cl>[CH:29]([S:26]([C:23]1[CH:24]=[CH:25][C:20]([C:18]2[CH:19]=[C:14]([C:12]3[O:11][N:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][NH:51][CH3:50])=[CH:4][CH:5]=4)[CH:13]=3)[C:15]([NH:32][C:40](=[O:41])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[N:16][CH:17]=2)=[N:21][CH:22]=1)(=[O:27])=[O:28])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 68104457HCID 68104457, compound

Product 1

HCID 68088960HCID 68088960, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl N-[3-[3-[4-(bromomethyl)phenyl]isoxazol-5-yl]-5-(5-isopropylsulfonyl-2-pyridyl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (275.5 mg, 0.3861 mmol) was taken into ethanol (1 mL)/DCM (1 mL) and this solution added to stirred methylamine (3.634 g, 38.61 mmol) in an sealed tube. The reaction was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with DCM and washed with saturated aqueous NaHCO3/brine (1:1, ×2), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 24 g column, eluting with 0 to 10% MeOH/DCM, loaded in DCM) to give the sub-title product as a beige solid (105.4 mg, 48% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.23 (d, 6H), 1.32 (s, 9H), 2.30 (s, 3H), 3.62 (sept, 1H), 3.72 (s, 2H), 7.46 (s, 1H), 7.50 (d, 2H), 7.87 (d, 2H), 8.40 (dd, 1H), 8.49 (d, 1H), 8.91 (d, 1H), 9.11 (d, 1H), 9.28 (d, 1H) and 10.06 (br s, 1H) ppm; MS (ES+) 564.2.

Workup

  1. additionthis solution added
  2. washwashed with saturated aqueous NaHCO3/brine (1:1, ×2)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (ISCO Companion™, 24 g column, eluting with 0 to 10% MeOH/DCM, loaded in DCM)

Sources & evidence

ORD record
ord-0e99e854e7004732be8dce3fe1ff742b
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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