Diisopropylethylamine → HCID 24856993, compound

HRID 1929942Notes

Reaction equation

HRID 1929942 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[N:10][CH:11]=[C:12]([C:14](=[O:23])[NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[OH:22])[CH:13]=2)=[CH:4][CH:3]=1.CN(C(O[N:40]1N=N[C:42]2[CH:43]=[CH:44]C=C[C:41]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:41]([NH:40][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:13][C:12]([C:14]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:23])=[CH:11][N:10]=1)=[O:30])[CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67505370HCID 67505370, compound

Product 1

HCID 24856993HCID 24856993, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[3-(4-Chloro-phenyl)-5-((1R,2R)-2-hydroxy-cyclohexylcarbamoyl)-pyridin-2-yloxy]-pentanoic acid (20 mg) was dissolved in DMF (1 mL). To the solution was added TBTU (16 mg), N,N-diisopropylethyl amine (0.038 mL, 42) and (N)-butylamine (0.005 mL). The reaction mixture was stirred for 16 h at room temperature. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica (dichloromethane/methanol gradient) to yield 21 mg of the title compound as a white solid, MS (ISP) 502.1, 504.1 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by column chromatography on silica (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-9fe7500ab64842d7b37288a72251f5c8
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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