Dimethylformamide → HCID 68410975, compound

HRID 1443486Notes

Reaction equation

HRID 1443486 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[C:25]([CH3:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[N:21]=3)[CH2:16][CH:15]2C(O)=O)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.CN(C(ON1N=N[C:63]2[CH:64]=[CH:65][CH:66]=N[C:62]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:77][N:78]([CH:80]=[O:81])[CH3:79]>>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[C:25]([CH3:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[N:21]=3)[CH2:16][CH:15]2[C:80](=[O:81])[N:78]([CH2:79][CH2:66][CH2:65][CH2:64][CH:63]=[CH2:62])[CH3:77])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68411844HCID 68411844, compound

Product 1

HCID 68410975HCID 68410975, compoundYield 70%

Procedure

The acid 134 (723 mg, 1.227 mmol) was dissolved in DMF (25 mL). Diisopropyl ethylamine (633 mg, 4.91 mmol) was added and the reaction mixture was placed on an ice-bath. N-methyl-1-hexen hydrochloride (266 mg, 1.78 mmol) and HATU (676 mg, 1.78 mmol) were added and the mixture was stirred at room temperature for 1 h. The solvent was removed and the residue was partitioned between EtOAc and aqueous sodium bicarbonate. The organic phase was collected and the crude product was purified by column chromatography (silica gel, Heptane/EtOAc 80:20→50:50). Evaporation of the solvent gave the title compound (585 mg, 70%). MS (M+H)+ 685.

Workup

  1. customthe reaction mixture was placed on an ice-bath
  2. customThe solvent was removed
  3. customthe residue was partitioned between EtOAc and aqueous sodium bicarbonate
  4. customThe organic phase was collected
  5. customthe crude product was purified by column chromatography (silica gel, Heptane/EtOAc 80:20→50:50)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e9e2df2285e44dcb8d90e89eae13bdd0
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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