Trifluoroacetic acid → HCID 86596927, compound

HRID 495140Notes

Reaction equation

HRID 495140 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[O:16][C:15](=[O:24])[CH:14]=1.CCN(C(C)C)C(C)C.Cl.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[O:16][C:15](=[O:24])[CH:14]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][NH:8][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)[C:18]=2[CH:19]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9795003HCID 9795003, compoundHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 86596927HCID 86596927, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The trifluoroacetic acid salt of 4-(3-amino-propoxy)-6-chloro-1-benzopyran-2-one (0.272 mmol, 0.10 g) is dissolved in 3 mL of DCM and is added enough DIEA to bring the pH to ˜9 as measured by wet pH paper. Isonicotinoyl chloride hydrochloride is added (0.50 mmol, 0.089 g) and the reaction is stirred at ambient temperature overnight. The reaction mixture is evaporated under reduced pressure and the crude material is purified by HPLC to obtain the title compound as the trifluoroacetic acid salt (39 mg, 30%). 1H NMR (DMSO-d6, 300 MHz) δ 8.93 (1H, br t), 8.73 (2H, br d), 7.80 (2H, m), 7.76 (1H, d, J=2.5 Hz), 7.69 (1H, dd, J=2.5, 8.75 Hz), 7.45 (1H, d, J=8.75 Hz), 5.97 (1H, s), 4.31 (2H, t, J=5.75 Hz), 3.51 (2H, q, J=6.5 Hz), 2.11 (2H, m); MS (ESI, Pos.) calcd for C18H15ClN2O4 m/z [M+H]=359.1, found 359.1.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customthe crude material is purified by HPLC

Sources & evidence

ORD record
ord-c75b64270a8648b5b0bfaa14a4b1cc4f
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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