Diisopropylethylamine → HCID 178425855, compound

HRID 1455156Notes

Reaction equation

HRID 1455156 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([C:16]#[N:17])[N:10]=[C:9]1[CH:18]([N:22]([CH2:32][CH2:33][NH2:34])[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:36]1([C:41](N)=[NH:42])C=CC=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([C:16]#[N:17])[N:10]=[C:9]1[CH:18]([N:22]([CH2:32][CH2:33][NH:34][C:41]([NH2:42])=[NH:36])[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 21076831HCID 21076831, compound

Product 1

HCID 178425855HCID 178425855, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[1-(1-benzyl-4-cyano-5-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-N-(2-amino-ethyl)-4-methyl-benzamide (75 mg, 0.16 mMol) in DMF (1.5 mL) was added 1H-pyrazole-1-carboxamidine hydrochloride (25 mg, 0.17 mMol) and diisopropylethyl amine (57 μL, 0.33 mMol). The reaction was stirred at RT for 16 h, quenched with water (2 mL) and diluted with methylene chloride (2 mL). The aqueous layer was adjusted to pH 7 and extracted with methylene chloride (2×5 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated. Purification of the residue by reverse phase HPLC furnished the title compound (38 mg, 37%) as a white powder. MS (ES) m/e 500.4 (M+H)+.

Workup

  1. customquenched with water (2 mL)
  2. additiondiluted with methylene chloride (2 mL)
  3. extractionextracted with methylene chloride (2×5 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by reverse phase

Sources & evidence

ORD record
ord-b45319f888db4285a57c4df65bd62a37
Source dataset
uspto-grants-2009_01
Patent number
US07482343B2

Reaction notes

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