Diisopropylethylamine → HCID 58558080, compound

HRID 1969693Notes

Reaction equation

HRID 1969693 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]=4[N:14]=[CH:15][C:10]3=[N:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.[N:28]1([C:33](=N)[NH2:34])C=CC=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:24][Si:23]([CH3:26])([CH3:25])[CH2:22][CH2:21][O:20][CH2:19][N:16]1[C:13]2[N:14]=[CH:15][C:10]3[N:11]([C:7]([CH:4]4[CH2:3][CH2:2][N:1]([C:33](=[NH:28])[NH2:34])[CH2:6][CH2:5]4)=[CH:8][N:9]=3)[C:12]=2[CH:18]=[CH:17]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 58558117HCID 58558117, compound

Product 1

HCID 58558080HCID 58558080, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-(piperidin-4-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.100 g, 0.269 mmol, Preparation #DDDDD.1), 1H-pyrazole-1-carboximidamid, hydrochloride (0.118 g, 0.807 mmol) and DIEA (0.188 mL, 1.08 mmol) in DMF (2 mL) was stirred at rt for about 72 h. The reaction mixture was purified by RP-HPLC (Table 1, Method 1) to give 4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboximidamide (0.037 g, 33%) as a brown oil: LC/MS (Table 1, Method b) Rt=1.82 min; MS m/z: 414 (M+H)+.

Workup

  1. customThe reaction mixture was purified by RP-HPLC (Table 1, Method 1)

Sources & evidence

ORD record
ord-8b9ad21525274c9a9466f47c22ee2248
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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