Diisopropylethylamine → HCID 51035143, compound

HRID 908237

Reaction equation

HRID 908237 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:15]=[N:14][N:13]([CH3:16])[C:12]=1[C:17]([OH:19])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:42]1([C:48]2[N:49]=[C:50]3[CH:55]=[C:54]([NH2:56])[N:53]=[CH:52][N:51]3[CH:57]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C>[C:42]1([C:48]2[N:49]=[C:50]3[CH:55]=[C:54]([NH:56][C:17]([C:12]4[N:13]([CH3:16])[N:14]=[CH:15][C:11]=4[Cl:10])=[O:19])[N:53]=[CH:52][N:51]3[CH:57]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4040512-Phenylimidazo[1,2-c]pyrimidin-7-amineHCID 6708234-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 51035143HCID 51035143, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF (8 ml) and diisopropylethylamine (738 mg) were added to 4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (916 mg, 5.7 mmol) and TBTU (1.83 g), and the mixture was stirred at r.t. (10 min). 2-Phenyl-imidazo[1,2-c]pyrimidin-7-ylamine (400 mg, 1.9 mmol) was added and the mixture was stirred at r.t. overnight. The reaction mixture was then poured on water (35 ml), and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and evaporated. The title compound (45 mg, 6.7%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40), followed by preparative, inverse-phase HPLC (Agilent Zorbax XdB-C18 column, time per run ˜7 min, flow rate 30 ml/min, solvent gradient H2O/CH3CN=95:5-5:95). MS (m/e)=353.1 [M+H+].

Workup

  1. stirringthe mixture was stirred at r.t. overnight
  2. additionThe reaction mixture was then poured on water (35 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ea3e772086db4ab793565cd66e7b98b5
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Linked notes

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