Diisopropylethylamine → HCID 86627062, compound

HRID 505801Notes

Reaction equation

HRID 505801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14](O)=[O:15])[C:11]3[C:17]([CH:24]=[O:25])=[C:18]([C:20]([O:22][CH3:23])=[O:21])[S:19][C:10]=3[C:9]=2[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:4][CH:3]=1.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.[CH:65]([N:68]1[CH2:72][CH2:71][CH:70]([NH:73][CH3:74])[CH2:69]1)([CH3:67])[CH3:66]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][C:14]([N:73]([CH:70]3[CH2:71][CH2:72][N:68]([CH:65]([CH3:67])[CH3:66])[CH2:69]3)[CH3:74])=[O:15])[C:11]3[C:17]([CH:24]=[O:25])=[C:18]([C:20]([O:22][CH3:23])=[O:21])[S:19][C:10]=3[C:9]=2[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:6][CH:7]=1

Participants

6

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 19819753HCID 19819753, compoundHCID 86627063HCID 86627063, compound

Product 1

HCID 86627062HCID 86627062, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution (0.13 M) of [5-(4-chlorophenyl)-6-cyclohexyl-3-formyl-2-(methoxycarbonyl)-4H-thieno[3,2-b]pyrrol-4-yl]acetic acid in DMF was treated with DIEA (3 eq.), HATU (1.5 eq.) and a solution (0.5 M) of 1-isopropyl-N-methylpyrrolidin-3-amine (1.5 eq.) in DMF. The reaction mixture was stirred at RT for 3 h. The reaction was quenched with aqueous NaHCO3 (saturated solution) and extracted with AcOEt. The combined organic phase was washed with brine and dried. Evaporation under reduced pressure gave a residue that was purified by flash chromatography on silica gel (1:49 Et3N/AcOEt) to afford the title compound (62%) as a solid.

Workup

  1. customThe reaction was quenched with aqueous NaHCO3 (saturated solution)
  2. extractionextracted with AcOEt
  3. washThe combined organic phase was washed with brine
  4. customdried
  5. customEvaporation under reduced pressure
  6. customgave a residue that
  7. customwas purified by flash chromatography on silica gel (1:49 Et3N/AcOEt)

Sources & evidence

ORD record
ord-d6ca983ed9e141779c24d93a61d7988f
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

Loading…