1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21057871, compound

HRID 2216287Notes

Reaction equation

HRID 2216287 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]([C:15]([OH:17])=O)=[CH:5][N:4]=1)#[N:2].[CH3:18][C:19]1[CH:20]=[C:21]([NH2:30])[N:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:23]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH3:18][C:19]1[CH:20]=[C:21]([NH:30][C:15]([C:6]2[C:7]([NH:9][CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[N:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[O:17])[N:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:23]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 708015-Amino-3-methyl-1-phenylpyrazoleHCID 757711-HydroxybenzotriazoleHCID 21941882HCID 21941882, compound

Product 1

HCID 21057871HCID 21057871, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2-Cyano-4-(2,2-dimethyl-propylamino)-pyrimidine-5-carboxylic acid (150 mg, 0.640 mmol), 5-Methyl-2-phenyl-2H-pyrazol-3-ylamine (211 mg, 1.28 mmol) and 1-hydroxybenzotriazole (147 mg, 1.28 mmol) in DMF (5 ml) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (199 mg, 1.28 mmol) at ambient temperature. After being stirred for 15 hours at ambient temperature, the reaction mixture is diluted with ethyl acetate, washed with saturated NaHCO3, dried over MgSO4 and concentrated. The crude product is purified by reverse-phase HPLC to give the product. Rf=0.44 (n-hexane:AcOEt=1:1). 1H NMR (400 MHz, CDCl3) δ 0.98(s, 9H), 2.33(s, 3H), 3.37(d, 2H), 6.55(s, 1H), 7.41-7.53(m,5H), 8.24(s, 1H), 9.01(br, 1H).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product is purified by reverse-phase HPLC
  5. customto give the product

Sources & evidence

ORD record
ord-b2dc77d5d6714e34812a7b4057dadaef
Source dataset
uspto-grants-2006_09
Patent number
US07112589B2

Reaction notes

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