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Water → HCID 66965069, compound

HRID 1515002
Notes
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Reaction equation

HRID 1515002 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[CH3:22][O:23][C:24](=[O:37])[CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([CH:34]=O)=[C:29]([CH3:36])[CH:28]=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.CCOC(C)=O>[CH3:22][O:23][C:24](=[O:37])[CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([C:34]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:18]=[CH:19][C:20]=3[N:21]=2)=[C:29]([CH3:36])[CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 2733225Ytterbium triflateHCID 669657403,4-diamino-N-quinolin-2-yl-benzamideHCID 86651272(4-Formyl-3,5-dimethylphenoxy)-acetic acid methyl ester

Product 1

HCID 66965069HCID 66965069, compound

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-diamino-N-quinolin-2-yl-benzamide (770 mg, 2.77 mmol) and (4-formyl-3,5-dimethylphenoxy)-acetic acid methyl ester (615 mg, 2.77 mmol) in DMSO (10 mL) was added Yb(OTf)3 (344 mg, 0.55 mmol) and the mixture was stirred at ambient temperature overnight. The reaction mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (1:4) as eluent gave {3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester as a white solid. MS (m/z) 481.4 (M+1); 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (m, 3H), 8.04 (d, 1H), 7.92 (d, 2H), 7.75 (m, 2H), 7.54 (m, 1H), 6.80 (s, 2H), 4.78 (s, 2H), 3.81 (s, 3H), 2.17 (s, 6H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-390abcac99f44342924c4b424110a8dd
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08222248B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes