(R)-Tetrahydro-3-furoic acid → HCID 67281103, compound

HRID 1958183Notes

Reaction equation

HRID 1958183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:20])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.[O:21]1[CH2:25][CH2:24][CH:23]([C:26](O)=[O:27])[CH2:22]1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([NH:20][C:26]([CH:23]3[CH2:24][CH2:25][O:21][CH2:22]3)=[O:27])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:17])([F:18])[F:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4661317(R)-Tetrahydro-3-furoic acidHCID 672813155-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine

Product 1

HCID 67281103HCID 67281103, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized in analogy to Example 42 g, using 5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine (example E) and tetrahydro-3-furancarboxylic acid, (CAN 89364-31-8) as starting materials; enantiomers were separated by chiral HPLC (ChiralPak AD, 30% ethanol/n-heptane (+) enantiomer isolated; LC-MS (UV peak area/ESI) 98.1%, 401.0869 (M+H)+; αD20 (MeOH)=+10.1°

Workup

  1. customenantiomers were separated by chiral HPLC (ChiralPak AD, 30% ethanol/n-heptane (+)
  2. customenantiomer isolated

Sources & evidence

ORD record
ord-3a813934c3094039a37db061e1fc2624
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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