Diisopropylethylamine → HCID 89462486, compound

HRID 1473180Notes

Reaction equation

HRID 1473180 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][O:20][C:21](=[O:25])[CH2:22][NH:23][CH3:24].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.[Cl-].[Na+].O>[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]1[C:15]([N:23]([CH2:22][C:21]([O:20][CH3:19])=[O:25])[CH3:24])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12140098HCID 12140098, compound

Product 1

HCID 89462486HCID 89462486, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-benzyl-3-cyano-1H-pyrrole-2-carboxylic acid (7.3 g, 32.4 mmol) in N,N-Dimethylformamide (DMF) (100 mL) was treated with sarcosine methyl ester hydrochloride (12 g, 86 mmol) and DIPEA (30 mL, 172 mmol), followed by HATU (26 g, 68.4 mmol). The mixture was stirred at 40° C. for 1 hour. The mixture was cooled to room temperature, brine was added and the resultant was extracted with ethyl acetate. The combined extracts were washed with HCl (1M), followed by brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford methyl 2-(1-benzyl-3-cyano-N-methyl-1H-pyrrole-2-carboxamido)acetate (9.2 g, 29.6 mmol, 91% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.31-7.38 (m, 3H). 7.20-7.26 (m, 2H) 6.73-6.78 (m, 1H) 6.40-6.46 (m, 1H) 5.17-5.26 (s, 2H) 4.16-4.26 (s, 2H) 3.71-3.80 (s, 3H) 3.06-3.15 (s, 3H); LCMS (m/z) ES+=312 (M+1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe resultant was extracted with ethyl acetate
  3. washThe combined extracts were washed with HCl (1M)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-52616395ea724b038c734042deed5158
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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