Diisopropylamine → HCID 69849496, compound

HRID 352230Notes

Reaction equation

HRID 352230 reaction equation
[C:1]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([N:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([C:27](O)=[O:28])[C:21]=3[C:20]3=[N:30][O:31][C:32]([CH3:33])=[C:19]3[C:18]2=[O:34])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:37]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-].C(NC(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[C:1]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([N:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([C:27]([NH2:37])=[O:28])[C:21]=3[C:20]3=[N:30][O:31][C:32]([CH3:33])=[C:19]3[C:18]2=[O:34])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 22714071HCID 22714071, compound

Product 1

HCID 69849496HCID 69849496, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 598, (0.05 g, 0.11 mmol), EDCI (0.032 g, 0.165 mmol), and HOBt (0.023 g, 0.165 mmol) in DMF (1.5 ml) under N2 was added NH4Cl (0.009 g, 0.165 mmol) and diisopropylamine (0.046 ml, 0.33 mmol). The reaction was stirred overnight. The mixture was diluted with EtOAc, washed (1.0 N HCl saturated with NaCl), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/EtOAc gradient) gave the title compound (0.024 g, 48%). MS(ES+) (m/z) 459.1 [M+1].

Workup

  1. washwashed (1.0 N HCl saturated with NaCl)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b85356ce19844a83a53462b3eb3377a9
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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