Triphenylphosphine → HCID 89691175, compound

HRID 2203100Notes

Reaction equation

HRID 2203100 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[F:22][CH2:23][C:24]1[N:25]=[C:26]([CH2:29]O)[S:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>O.C1COCC1>[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:29][C:26]5[S:27][CH:28]=[C:24]([CH2:23][F:22])[N:25]=5)=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 89690274HCID 89690274, compoundHCID 896910841-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 89691175HCID 89691175, compoundYield 2.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg), (4-(fluoromethyl)thiazol-2-yl)methanol (105 mg), triphenylphosphine (280 mg) and THF (5 ml) was added bis(2-methoxyethyl) azodicarboxylate (250 mg), and the mixture was stirred at room temperature for 2 h, then at 70° C. for 2 h. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (EtOAc/MeOH) to give the title compound (4.0 mg) as a white solid.

Workup

  1. waitat 70° C. for 2 h
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel column chromatography (EtOAc/MeOH)

Sources & evidence

ORD record
ord-80bc6d044e9842309ef78093582a8a13
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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