Diisopropylethylamine → HCID 135800728, compound

HRID 1247778Notes

Reaction equation

HRID 1247778 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:11]=[N:10][N:9]2[CH2:12][CH2:13][NH:14][C:8]=12.C(N(C(C)C)C(C)C)C.[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][C:34](ON1C(=O)CCC1=O)=[O:35])=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][C:34]([NH:6][C:7]1[CH:11]=[N:10][N:9]2[CH2:12][CH2:13][NH:14][C:8]=12)=[O:35])=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10684599Boc-Beta-Ala-OSuHCID 1358007252,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-amine sulfate

Product 1

HCID 135800728HCID 135800728, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazole sulfuric acid salt (2.22 g) and N-ethyldiisopropylamine (2.84 g) in methylene chloride (70 ml) was added N-[3-(tert-butoxycarbonylamino)propionyloxy]succinimide (3.15 g). The mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The oily residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform to give 7-[3-(tert-butoxycarbonylamino)propionyl]amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (2.2 g) as a solid.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-e112db3312f442418e87c290c9d8517b
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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