Diisopropylethylamine → HCID 5279908, compound

HRID 1394427Notes

Reaction equation

HRID 1394427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([C:11](=[O:15])[C:12]([OH:14])=O)=[CH:9][NH:10][C:3]=12.[C:16]1([C:22](=[C:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:23]#[N:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.C(N(C(C)C)C(C)C)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([C:11](=[O:15])[C:12]([N:28]3[CH2:27][CH2:26][C:25](=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:23]#[N:24])[CH2:30][CH2:29]3)=[O:14])=[CH:9][NH:10][C:3]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 22476293HCID 22476293, compoundHCID 59681564Phenyl(piperidin-4-ylidene)acetonitrile

Product 1

HCID 5279908HCID 5279908, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-oxo-acetic acid (1.5 g, 6.7 mmol) and phenylpiperidine-4-ylidene acetonitrile (1.3 g, 6.7 mmol) in DMF (50 mL) was added DEPBT (3.15 g, 10.5 mmol) and ethyl diisopropylamine (6.1 mL, 35 mmol). The solution was stirred 20 h, concentrated under vacuum and partitioned between 5% Na2CO3(aq) (80 mL) and EtOAc (5×100 mL). The combine organic layers were dried (MgSO4), filtered and concentrated. The residue was purified by Biotage Chromatography (SiO2, 30% EtOAc/Hex to 100% EtOAc) and by preparative HPLC to yield the title compound (300 mg, 0.74 mmol, 11%) as a yellow solid.

Workup

  1. concentrationconcentrated under vacuum
  2. custompartitioned between 5% Na2CO3(aq) (80 mL) and EtOAc (5×100 mL)
  3. dry with materialThe combine organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Biotage Chromatography (SiO2, 30% EtOAc/Hex to 100% EtOAc) and by preparative HPLC

Sources & evidence

ORD record
ord-259ed961c2344ee9842dcbb718c72660
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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