Diisopropylethylamine → N-{2-[4-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonylamino]-2-oxoethyl}-N'-(2,2-dimethylpropionyloxy)-2-isobutylmalonamide

HRID 1516473Notes

Reaction equation

HRID 1516473 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([CH:21]=[O:22])=[C:19]([Cl:23])[N:18]=[C:17]2[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:11][CH:10]=1)(=[O:8])=[O:7])=[O:4].[CH3:28][C:29]([CH3:45])([CH3:44])[C:30]([O:32][NH:33][C:34]([CH:36]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:37](O)=[O:38])=[O:35])=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:24]([C:17]1[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][C:37](=[O:38])[CH:36]([CH2:40][CH:41]([CH3:42])[CH3:43])[C:34]([NH:33][O:32][C:30](=[O:31])[C:29]([CH3:44])([CH3:45])[CH3:28])=[O:35])(=[O:7])=[O:8])=[CH:10][CH:11]=2)[C:20]([CH:21]=[O:22])=[C:19]([Cl:23])[N:18]=1)[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57931395N-(2-Aminoacetyl)-4-(2-butyl-4-chloro-5-formyl-imidazol-1-ylmethyl)benzenesulfonamideHCID 594288372-(2,2-Dimethylpropionyloxycarbamoyl)-4-methylpentanoic acid

Product 1

HCID 86635446N-{2-[4-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonylamino]-2-oxoethyl}-N'-(2,2-dimethylpropionyloxy)-2-isobutylmalonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2-Aminoacetyl)-4-(2-butyl-4-chloro-5-formyl-imidazol-1-ylmethyl)benzenesulfonamide (770 mg, 1.2 mmol, 1.0 eq) and 2-(2,2-Dimethylpropionyloxycarbamoyl)-4-methylpentanoic acid (360 mg, 1.2 mmol, 1.0 eq) were dissolved in 13 mL DMF. HATU (460 mg, 1.2 mmol, 1.0 eq) was then added followed by DIPEA (630 μL, 3.6 mmol, 3.0 eq) and the mixture was stirred at room temperature. After 3 hours, the mixture was diluted with 30 mL EtOAc, washed with 20 mL 10% aq. LiCl solution, water, saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure to yield crude intermediate 3a. MS m/z: [M+H+] calcd for C29H40ClN5O8S, 654.2; found 654.4.

Workup

  1. washwashed with 20 mL 10% aq. LiCl solution, water, saturated aqueous NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d556306b622843aba92956fd6eee003e
Source dataset
uspto-grants-2012_07
Patent number
US08227497B2

Reaction notes

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