Diisopropylethylamine → HCID 69289368, compound

HRID 2375792Notes

Reaction equation

HRID 2375792 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[C:8]([CH3:16])=[C:9]([C:13]([OH:15])=O)[NH:10][C:11]=1[CH3:12])=[O:4].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.Cl.Cl.[CH:52]([N:55]1[CH2:60][CH2:59][CH:58]([NH2:61])[CH2:57][CH2:56]1)([CH3:54])[CH3:53]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]1[C:8]([CH3:16])=[C:9]([C:13](=[O:15])[NH:61][CH:58]2[CH2:59][CH2:60][N:55]([CH:52]([CH3:54])[CH3:53])[CH2:56][CH2:57]2)[NH:10][C:11]=1[CH3:12]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 108468134-(2-METHOXYCARBONYL-ETHYL)-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACIDHCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochloride

Product 1

HCID 69289368HCID 69289368, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

263 mg of (1.17 mmol) 4-(2-methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid were dissolved in DMF (10 mL). 488.4 mg (1.28 mmol) of HATU and DIEA (224 μl) were added and the resulting mixture was stirred for 45 minutes at RT. A solution of 276.3 mg (1.28 mmol) of 1-isopropyl-piperidine-4-ylamine-dihydrochloride and 448 μl of DIEA was added. The reaction mixture was stirred over night after which it was concentrated. The residue was diluted with DCM and washed with a saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated. Preparative HPLC(CH3CN/H2O gradient+0.05% formic acid) gave pure 3-[5-(1-isopropyl-piperidin-4-ylcarbamoyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid methyl ester (166 mg) as a colorless amorphous material. MS (ESI+): m/e=351 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred over night after which it
  2. concentrationwas concentrated
  3. additionThe residue was diluted with DCM
  4. washwashed with a saturated NaHCO3 solution and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d6470a8dc5f4e32b5d88017b3cb7564
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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