Diisopropylethylamine → HCID 57418378, compound

HRID 1868155Notes

Reaction equation

HRID 1868155 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([N:23]4[CH2:28][CH2:27][CH:26]([C:29]([OH:31])=O)[CH2:25][CH2:24]4)[CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[C@H:10]([CH3:32])[CH2:9]2)=[C:4]([C:33]([F:36])([F:35])[F:34])[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:55]([CH3:57])[CH3:56])C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([N:23]4[CH2:24][CH2:25][CH:26]([C:29]([N:55]([CH3:57])[CH3:56])=[O:31])[CH2:27][CH2:28]4)[CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[C@H:10]([CH3:32])[CH2:9]2)=[C:4]([C:33]([F:34])([F:36])[F:35])[CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68553155HCID 68553155, compound

Product 1

HCID 57418378HCID 57418378, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[3-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenyl]piperidine-4-carboxylic acid (200 mg, 0.38 mmol) in DMF (4.0 mL) was added BOP (202 mg, 0.46 mmol), DIPEA (0.33 mL, 1.9 mmol), and finally N′N-dimethylamine (0.6 mL, 1.1 mmol). The reaction was allowed to stir at ambient temperature over a 16 hour period, after which it was judged complete by LCMS. The reaction mixture was diluted with EtOAc (50 mL), and washed with saturated NaHCO3(aq) (3×25 mL). The organic layer was dried over Na2SO4, decanted, and concentrated in vacuo. The resultant crude oil was purified on a normal phase SiO2 column (20%-80% EtOAc/Hexanes) affording the desired amide in >95% purity. HRMS: calcd for C26H32F4N4O3S+H+, 557.22040. found ([M+H]+), 557.22195.

Workup

  1. washwashed with saturated NaHCO3(aq) (3×25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude oil was purified on a normal phase SiO2 column (20%-80% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-714f336ffa244d77a0555925b961ec6b
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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