Diisopropylethylamine → HCID 16128497, compound

HRID 747096Notes

Reaction equation

HRID 747096 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)=[C:4]2[NH:13][CH:14]=[C:15]([C:16](=[O:20])[C:17]([OH:19])=O)[C:3]=12.[C:21]1([C:27](=[N:34][C:35]#[N:36])[N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+].O>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)=[C:4]2[NH:13][CH:14]=[C:15]([C:16](=[O:20])[C:17]([N:31]3[CH2:30][CH2:29][N:28]([C:27](=[N:34][C:35]#[N:36])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:33][CH2:32]3)=[O:19])[C:3]=12

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 58806128HCID 58806128, compoundHCID 58852074HCID 58852074, compound

Product 1

HCID 16128497HCID 16128497, compoundYield 3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-(4-fluoro-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (100 mg), (phenyl(piperazin-1-yl)methylene)cyanamide (77 mg), DEPBT (108 mg) and iPr2NEt (0.2 ml) were combined in DMF (2 ml). The reaction mixture was stirred at room temperature for 17 hours before diluted with 10% Na2CO3 in water (5 ml). The aqueous solution was extracted with EtOAc (3×20 ml). The organic layer was combined, dried over MgSO4 and concentrated. The residue was tritarated with MeOH (5 ml) and the resultant solid was collected by filtration to give ((4-(2-(4-fluoro-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetyl)piperazin-1-yl)(phenyl)methylene)cyanamide (5 mg).

Workup

  1. extractionThe aqueous solution was extracted with EtOAc (3×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-09024915de214605aa3552989c689ddc
Source dataset
uspto-grants-2008_07
Patent number
US07396830B2

Reaction notes

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