Formic Acid → HCID 23145394, compound

HRID 13272Notes

Reaction equation

HRID 13272 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[NH2:40])[O:5][C:6]1[C:7]([CH:29]2[CH2:33][CH2:32][CH2:31][N:30]2[C:34](=[O:36])[CH3:35])=[CH:8][C:9]2[N:13](COCC[Si](C)(C)C)[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:11][C:10]=2[CH:28]=1.[CH:41](O)=O>>[N:40]1[C:39]2[CH:38]=[CH:37][C:4]([O:5][C:6]3[C:7]([CH:29]4[CH2:33][CH2:32][CH2:31][N:30]4[C:34](=[O:36])[CH3:35])=[CH:8][C:9]4[NH:13][C:12]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)=[N:11][C:10]=4[CH:28]=3)=[CH:3][C:2]=2[NH:1][CH:41]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 23145252HCID 23145252, compound

Product 1

HCID 23145394HCID 23145394, compound

Conditions

Temperature
100 °C

Procedure

19 mg of 1-(2-(6-(3,4-diamino-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone obtained in Example 155 (step 2) was dissolved in 1 ml of formic acid, and the reaction liquid was stirred at 100° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid] to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  5. customto obtain the entitled compound

Sources & evidence

ORD record
ord-fb658565146749b48b78aa5f7b5482ec
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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