Water → HCID 67019951, compound

HRID 1673246Notes

Reaction equation

HRID 1673246 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[N:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:12]=2)[O:7][C:6]([CH3:30])([CH3:29])[CH2:5]1)=[N+]=[N-].O.CP(C)C>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH:12]=[C:13]3[C@H:4]([NH2:1])[CH2:5][C:6]([CH3:30])([CH3:29])[O:7][C:8]3=[N:9][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 86622724HCID 86622724, compound

Product 1

HCID 67019951HCID 67019951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of Step A (9.5 g, 20.7 mmol) in 50 mL of THF was added 2.5 mL of H2O and 31.0 mL of trimethylphosphine in THF (1.0 M, 31.0 mmol). After stirring at rt for 3 h, the solvent was evaporated. Chromatography on a Biotage 40+M cartridge using 1:19 v/v CH3OH/CH2Cl2 as the eluant afforded the product: 1H NMR δ 1.42 (s, 3H), 1.54 (s, 3H), 1.78 (t, J=12.5, 1H), 2.18 (dd, J=5.9, 13.4, 1H), 4.16 (dd, J=6.0, 11.7, 1H), 7.04 (d, J=8.5, 2H), 7.17-7.26 (m, 5H), 7.93 (s, 1H).

Workup

  1. customthe solvent was evaporated
  2. customafforded the product

Sources & evidence

ORD record
ord-0dba3b1a8f15487b9cd059586d03bece
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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