Diisopropylethylamine → HCID 11950959, compound

HRID 1766444Notes

Reaction equation

HRID 1766444 reaction equation
[CH2:1]([O:5][C:6]1[C:14]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[F:25])=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:57][C@@H:58]1[CH2:63][CH2:62][CH2:61][CH2:60][C@H:59]1[OH:64]>CN(C=O)C>[CH2:1]([O:5][C:6]1[C:14]([C:15]2[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=[CH:17][C:16]=2[F:25])=[CH:13][C:9]([C:10]([NH:57][C@@H:58]2[CH2:63][CH2:62][CH2:61][CH2:60][C@H:59]2[OH:64])=[O:12])=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21109717HCID 21109717, compound

Product 1

HCID 11950959HCID 11950959, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Butoxy-5-(2-fluoro-5-trifluoromethyl-phenyl)-nicotinic acid (0.10 g, 0.3 mmol) was dissolved in DMF (5 mL). To the solution was added TBTU (0.10 g, 0.3 mmol), N,N-diisopropylethyl amine (0.24 mL, 1.4 mmol) and (1R,2R)-2-amino-cyclohexanol (47 mg, 0.3 mmol). The reaction mixture was stirred for 18 h at room temperature. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 78 mg of the title compound as a light yellow solid, mp 172–178° C., MS (ISP) 455.3 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-ceeb2956c38240d5a2f7fb734e3b3c83
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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