Triethylamine → HCID 86605400, compound

HRID 1180432Notes

Reaction equation

HRID 1180432 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]([O:12][CH:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:14]1[CH:22]=[CH:21][C:17](C(O)=O)=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].Cl.CN[O:32][CH3:33].CN([C:37]([O:41][N:42]1N=NC2C=CC=N[C:43]1=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>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]([O:12][CH:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:14]1[CH:22]=[CH:21][C:17]([C:33]([N:42]([O:41][CH3:37])[CH3:43])=[O:32])=[CH:16][CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10429855HCID 10429855, compound

Product 1

HCID 86605400HCID 86605400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)oxy](phenyl)methyl]benzoic acid from example 46 (40 mg, 0.105 mmol) and N,O-dimethylhydroxylamine hydrochloride (10.3 mg, 0.105 mmol, 1 eq) in 1 mL DMF were added HATU (40 mg, 0.105 mmol, 1 eq), triethylamine (32 mg, 0.315 mmol, 3 eq). The mixture was stirred at room temperature for 18 hours, then poured into a half saturated solution of NaHCO3 (5 mL). It was extracted with EtOAc (2×10 mL); washed organic fraction with brine, concentrated to give the product.

Workup

  1. extractionIt was extracted with EtOAc (2×10 mL)
  2. concentrationwashed organic fraction with brine, concentrated
  3. customto give the product

Sources & evidence

ORD record
ord-c8de2906aab744a0b5f810c194ba8eb3
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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