Diisopropylethylamine → HCID 178502434, compound

HRID 1625528Notes

Reaction equation

HRID 1625528 reaction equation
[I:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([C@@H:9]3[CH2:13][C@H:12]([CH3:14])[CH2:11][NH:10]3)=[N:8][C:4]=2[CH:3]=1.[CH3:17][O:18][C:19]([NH:21][C@@H:22]([CH:26]([CH3:28])[CH3:27])[C:23](O)=[O:24])=[O:20].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.O>[I:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([C@@H:9]3[CH2:13][C@H:12]([CH3:14])[CH2:11][N:10]3[C:23]([C@@H:22]([NH:21][C:19](=[O:20])[O:18][CH3:17])[CH:26]([CH3:28])[CH3:27])=[O:24])=[N:8][C:4]=2[CH:3]=1

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 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 178461565HCID 178461565, compound

Product 1

HCID 178502434HCID 178502434, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 5-iodo-2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-benzimidazole (2.29 g, 7.00 mmol) and (2S)-2-(methoxycarbonylamino)-3-methyl-butanoic acid (1.49 g, 7.70 mmol) in DMF is added HATU (3.46 g, 9.1 mmol) and DIPEA (2.4 mL, 14.0 mmol) at rt. The reaction mixture is stirred at rt overnight. To the reaction mixture is added water (350 mL) with fast stirring upon which a white solid precipitated out. The solid is suction filtered and dried under vacuum to give methyl N-[(1S)-1-[(2S,4S)-2-(5-iodo-1H-benzimidazol-2-yl)-4-methyl-pyrrolidine-1-carbonyl]-2-methyl-propyl]carbamate (2.73 g, 81%).

Workup

  1. stirringwith fast stirring upon which a white solid
  2. customprecipitated out
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ba7fa9351693486f84bb80b6fc2c159b
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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