4-Methylmorpholine → HCID 11082168, compound

HRID 1457192Notes

Reaction equation

HRID 1457192 reaction equation
Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:14][C:15]1[C:19]([CH3:20])=[C:18]([NH:21][S:22]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[O:38][CH:39]=[CH:40][N:41]=4)=[CH:33][C:32]=3[CH2:42][NH:43][CH3:44])=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[O:17][N:16]=1.CN1CCOCC1.[F:52][C:53]([F:59])([F:58])[CH2:54][C:55](O)=[O:56].OC1C2N=NNC=2C=CC=1>CN(C=O)C>[CH3:14][C:15]1[C:19]([CH3:20])=[C:18]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:36]=[CH:35][C:34]([C:37]3[O:38][CH:39]=[CH:40][N:41]=3)=[CH:33][C:32]=2[CH2:42][N:43]([CH3:44])[C:55](=[O:56])[CH2:54][C:53]([F:59])([F:58])[F:52])(=[O:24])=[O:23])[O:17][N:16]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779723,3,3-Trifluoropropionic acidHCID 131720973HCID 131720973, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 11082168HCID 11082168, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (EDC, 50 mg; 0.26 mmol) was added to a solution of N-(3,4-dimethyl-5-isoxazolyl)-2'-[(methylamino)methyl]-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide, monohydrochloride (100 mg; 0.21 mmol, prepared as in Step (A) of Example 28), N-methylmorpholine (0.80 ml; 0.73 mmol), 3,3,3-trifluoropropionic acid (33 mg; 0.26 mmol), and hydroxybenzotriazole (HOBT, 40 mg; 0.26 mmol) in DMF at 0° C. After 18 hours at room temperature, the reaction mixture was partitioned between EtOAc (30 ml) and water (30 ml). The organic layer was washed with saturated KHSO4 (2×30 ml), water (30 ml), brine (30 ml), dried (MgSO4) and concentrated. The residue was chromatographed on a 2.5×12 cm silica gel column using 1000 ml EtOAc:Hex, 3:1 and 500 ml EtOAc as the mobile phase. The pure fractions were concentrated to afford 49 mg (43%) of the title compound of this Example as a white powder.

Workup

  1. customthe reaction mixture was partitioned between EtOAc (30 ml) and water (30 ml)
  2. washThe organic layer was washed with saturated KHSO4 (2×30 ml), water (30 ml), brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a 2.5×12 cm silica gel column
  6. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-27c81b96efe74d8fac9766baefc09eca
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

Loading…