Dimethylformamide → HCID 68686883, compound

HRID 1991422Notes

Reaction equation

HRID 1991422 reaction equation
CCN(C(C)C)[CH:4]([CH3:6])[CH3:5].[O:10]([CH2:17]C(Cl)=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O(CC(O)=O)[C:22]1C=CC=CC=1.CN(C([O:39][N:40]1[N:48]=[N:47][C:42]2[CH:43]=[CH:44][CH:45]=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:65][N:66]([CH:68]=[O:69])[CH3:67]>>[O:10]([CH2:17][C:68]([N:66]1[CH2:67][CH2:6][CH2:4][CH2:5][C@@H:65]1[C:41]1[N:46]=[C:45]([C:44]2[CH:43]=[CH:42][N:47]=[N:48][CH:22]=2)[O:39][N:40]=1)=[O:69])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 19188Phenoxyacetic AcidHCID 69703Phenoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 86612873HCID 86612873, compound

Product 1

HCID 68686883HCID 68686883, compound

Procedure

Crude material from step 3 was dissolved in 1 ml DMF and 0.1 mmol DIPEA. Either 0.1 mmol phenoxyacetyl chloride were added and the reaction stirred at room temperature for 30 min, or the corresponding phenoxyacetic acid derivatives were pre-activated with HATU/DIPEA in DMF for 10 min and added to the crude material from step 3. The product was isolated via preparative high performance liquid chromatography (HPLC).

Workup

  1. customThe product was isolated via preparative high performance liquid chromatography (HPLC)

Sources & evidence

ORD record
ord-63d2cbabdf6847de9cb2457d07fff208
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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