Diisopropylethylamine → HCID 58860841, compound

HRID 1350311Notes

Reaction equation

HRID 1350311 reaction equation
CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:25]1([S:28]([C:31]2[CH:36]=[CH:35][C:34](/[C:37](=[CH:41]\[CH:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)/[C:38](O)=[O:39])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH2:27][CH2:26]1.[NH2:48][C:49]1[CH:54]=[CH:53][C:52]([F:55])=[CH:51][N:50]=1>C(Cl)Cl>[CH:25]1([S:28]([C:31]2[CH:32]=[CH:33][C:34](/[C:37](=[CH:41]\[CH:42]3[CH2:43][CH2:44][O:45][CH2:46][CH2:47]3)/[C:38]([NH:48][C:49]3[CH:54]=[CH:53][C:52]([F:55])=[CH:51][N:50]=3)=[O:39])=[CH:35][CH:36]=2)(=[O:29])=[O:30])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27377012-Amino-5-fluoropyridineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 56971691(2E)-2-[4-(Cyclopropanesulfonyl)phenyl]-3-(oxan-4-yl)prop-2-enoic acid

Product 1

HCID 58860841HCID 58860841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFFH (283 mg, 1.07 mmol) and DIPEA (373 μmol, 2.14 mmol) were added to a stirred solution of (E)-2-(4-cyclopropanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid (Preparation 23, 300 mg, 0.89 mmol) in anhydrous CH2Cl2 (18 mL). After 30 min, the solution was treated portionwise with 2-amino-5-fluoropyridine (200 mg, 1.78 mmol) over 30 min, before being stirred further for 16 h. Solvent evaporation and purification by RP-HPLC furnished the title compound: RTA=3.34 min; m/z (ES+)=431.2 [M+H]+.

Workup

  1. customSolvent evaporation and purification by RP-HPLC

Sources & evidence

ORD record
ord-225acaf660234db882aedf047ddd302e
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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