Triethylamine → HCID 131735257, compound

HRID 627033Notes

Reaction equation

HRID 627033 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:14])[C@@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C@@H:16]([CH:33]([CH3:35])[CH3:34])[C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][CH:20]1[C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:31]([NH:30][C:28]([CH:20]1[N:19]([C:17](=[O:18])[C@@H:16]([NH:15][C:10](=[O:12])[C@@H:9]([N:8]([CH3:14])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:13])[CH:33]([CH3:34])[CH3:35])[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21]1)=[O:29])[CH3:32]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1178731111-[(2S)-2-Amino-3-methyl-1-oxobutyl]-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Product 1

HCID 131735257HCID 131735257, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid (40.9 mg, 201 μmol, Eq: 1.5) and 1-((S)-2-amino-3-methylbutanoyl)-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (39 mg, 134 μmol, Eq: 1.00) in DMF (1 mL) was added HATU (76.6 mg, 201 μmol, Eq: 1.5) followed by triethylamine (30 μL, 215 μmol, Eq: 1.6) and the resulting solution was stirred at rt for 2 h. The reaction was poured into saturated aqueous NaHCO3 (10 mL) and the mixture was extracted with EtOAc (10 mL). The EtOAc layer was concentrated in vacuo and the crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes) to give tert-butyl (2S)-1-((2S)-1-(2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (50 mg), m/z=476 (M+H).

Workup

  1. extractionthe mixture was extracted with EtOAc (10 mL)
  2. concentrationThe EtOAc layer was concentrated in vacuo
  3. customthe crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9b759e01eb9d45388128f8f4928e716a
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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