Triphenylphosphine → HCID 57785802, compound

HRID 1628620Notes

Reaction equation

HRID 1628620 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[N:7]([CH2:19][CH2:20][CH2:21][CH2:22]O)[C:6]=2[C:5]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:12]4[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=4)[CH2:22][CH2:21][CH2:20][CH2:19][N:7]3[C:6]=2[C:5]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68763610HCID 68763610, compound

Product 1

HCID 57785802HCID 57785802, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-chloro-2-[(4-chlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-ol (Reference Example 36; 200 mg, 0.48 mmol) and triphenylphosphine (186 mg, 0.71 mmol) in tetrahydrofuran (10 mL) was added diisopropyl azodicarboxylate (0.140 mL, 0.71 mmol) dropwise at 0° C. The mixture was warmed to room temperature and stirred for 24 hours followed by concentration in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/isopropyl ether to give the title compound (105 mg, 0.26 mmol, 54%) as a colorless solid.

Workup

  1. concentrationfollowed by concentration in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give the solid, which
  5. customwas recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-b06baa52cb1b471a9855ec9a31f6aa1f
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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