Triphenylphosphine → HCID 22490029, compound

HRID 2180138Notes

Reaction equation

HRID 2180138 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1[C:22]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([OH:36])=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[N:26][CH:25]=2)=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:37])[NH:18]2.[C:38]([CH2:40][N:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][CH2:49]O)[CH2:43][CH2:42]1)#[N:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:38]([CH2:40][N:41]1[CH2:42][CH2:43][N:44]([CH2:47][CH2:48][CH2:49][O:36][C:30]2[CH:29]=[C:28]3[C:33]([C:24]([O:23][C:22]4[C:14]([F:13])=[C:15]5[C:19](=[CH:20][CH:21]=4)[NH:18][C:17]([CH3:37])=[CH:16]5)=[CH:25][N:26]=[N:27]3)=[CH:32][C:31]=2[O:34][CH3:35])[CH2:45][CH2:46]1)#[N:39]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 21936040HCID 21936040, compound2×HCID 1357497764-(4-Fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline

Product 1

HCID 22490029HCID 22490029, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (0.095 ml, 0.6 mmol) was added dropwise to a suspension of 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline (0.1 g, 0.3 mmol), prepared as described in Example 4), 3-(4-cyanomethylpiperazin-1-yl)propan-1-ol (0.085 g, 0.45 mmol) and triphenylphosphine (0.155 g, 0.6 mmol) in methylene chloride (2.5 ml). The mixture was stirred for 30 minutes at ambient temperature. Further 3-(4-cyanomethylpiperazin-1-yl)propan-1-ol (0.085 g, 0.45 mmol), triphenylphosphine (0.155 g, 0.6 mmol) and diethyl azodicarboxylate (0.095 ml, 0.6 mmol) were added. The mixture was stirred for 30 minutes and the volatiles were removed under vacuum. The residue was purified by column chromatography eluting with ethylacetate/methylene chloride (1/1) followed by methanol/ethyl acetate/methylene chloride (5/45/50 followed by 10/40/50 and 10/0/90). The fractions containing the expected product were combined and evaporated to give 7-(3-(4-cyanomethylpiperazin-1-yl)propoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxycinnoline (0.035 g, 24%).

Workup

  1. customprepared
  2. stirringThe mixture was stirred for 30 minutes
  3. customthe volatiles were removed under vacuum
  4. customThe residue was purified by column chromatography
  5. washeluting with ethylacetate/methylene chloride (1/1)
  6. additionThe fractions containing the expected product
  7. customevaporated

Sources & evidence

ORD record
ord-44d2369bd853456186b8f7a6a2b30f81
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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