Ethyl Acetate → HCID 86647503, compound

HRID 389217Notes

Reaction equation

HRID 389217 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26])[C@H:15]([C:36](O)=[O:37])[CH2:14]2)=[CH:4][C:3]=1[O:39][CH3:40].CC[N:43](C(C)C)C(C)C.CN(C(ON1N=N[C:60]2[CH:61]=[CH:62]C=N[C:59]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:74][CH2:75][O:76][C:77]([CH3:79])=[O:78]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26])[C@H:15]([C:36]([NH:43][C@:79]3([C:77]([O:76][CH2:75][CH3:74])=[O:78])[CH2:62][C@H:61]3[CH:60]=[CH2:59])=[O:37])[CH2:14]2)=[CH:4][C:3]=1[O:39][CH3:40]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59571194HCID 59571194, compound

Product 1

HCID 86647503HCID 86647503, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step 2 (368 mg, 0.593 mmol), Intermediate A2 (136 mg, 0.712 mmol) and DIPEA (0.518 mL, 2.97 mmol) in DMF (10 mL) was added HATU (271 mg, 0.712 mmol). The solution was stirred at RT for 2 hours, diluted with EtOAc (150 mL), washed with water (3×50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 5% to 75% EtOAc in hexane, to give the title product (411 mg). LRMS (ESI) m/z 757.4 [(M+H)+; calcd for C37H50BrN4O8: 757.3].

Workup

  1. washwashed with water (3×50 mL), brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 5% to 75% EtOAc in hexane

Sources & evidence

ORD record
ord-a4c622686c5e453cb07f5bed6761c567
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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