HCID 71616872, compound → HCID 89656125, compound

HRID 930889Notes

Reaction equation

HRID 930889 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]3[CH:24]=[CH:23][NH:22][C:16]=3[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)=[O:7])=[CH:4][CH:3]=1.FC(F)(F)CS(NC1C=CC(OC2CCCOC2)=C(C2C3C=CNC=3C(=O)N(C)C=2)C=1)(=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH:6]([OH:7])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]3[CH:24]=[CH:23][NH:22][C:16]=3[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 71616872HCID 71616872, compoundHCID 89656430HCID 89656430, compound

Product 1

HCID 89656125HCID 89656125, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 139 (0.05 g, 0.138 mmol) and sodium tetrahydroborate (2) (5.21 mg, 0.138 mmol) in tetrahydrofuran (2 mL) was heated at 60° C. for 3 hours. The solvent was removed, and the residue was purified by reverse phase Preparative HPLC (10-80% acetonitrile in 0.1% TFA/water) to give the title compound (0.042 g, 0.115 mmol, 84% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.70 (s, 1H), 7.56 (d, J=7.63 Hz, 1H), 7.35-7.39 (m, 1H), 7.27-7.31 (m, 1H), 7.21-7.23 (m, 4H), 7.00 (d, J=8.54 Hz, 2H), 6.79 (s, 1H), 5.94 (t, J=2.29 Hz, 1H), 5.75 (s, 1H), 3.47 (s, 3H). MS (DCI+) m/z 365.0 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by reverse phase Preparative HPLC (10-80% acetonitrile in 0.1% TFA/water)

Sources & evidence

ORD record
ord-8be4b32f27e741d6ba8956550a11233e
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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