Dimethylamine → HCID 178462128, compound

HRID 1944754Notes

Reaction equation

HRID 1944754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:24]=[N:25][C:26](Cl)=[C:27]([Br:29])[CH:28]=3)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.C[CH2:32][N:33](C(C)C)[CH:34](C)C.CNC.C1COCC1>CN1C(=O)CCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:24]=[N:25][C:26]([N:33]([CH3:34])[CH3:32])=[C:27]([Br:29])[CH:28]=3)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 178462127HCID 178462127, compound

Product 1

HCID 178462128HCID 178462128, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Trans-4-(5-Bromo-6-chloro-pyridine-3-sulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 241, 300 mg, 0.580 mmol) was dissolved in NMP (3 ml). DIPEA (202 ul, 1.16 mmol) was added followed by dimethylamine in THF (2M, 0.87 ml, 1.74 mmol). The reaction mixture was microwaved at 160° C. for 15 min., after which LCMS indicated that the reaction was complete. The mixture was diluted with EtOAc and washed H2O. The organic layer was concentrated in vacuo and purified via column chromatography using a biotage SP1, 12+M column, with 50% EtOAc in heptane as calculated gradient to yield the title compound as a white solid (258 mg, 84%). MS MH+ 529.9

Workup

  1. customThe reaction mixture was microwaved at 160° C. for 15 min.
  2. washwashed H2O
  3. concentrationThe organic layer was concentrated in vacuo
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-fb058a99a5c440baa24e2e594e37fe23
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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