HCID 67421157, compound → HCID 67421153, compound

HRID 1509790Notes

Reaction equation

HRID 1509790 reaction equation
[O:1]=[C:2]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](=[O:34])(=[O:33])[NH2:32])=[CH:27][CH:26]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:1]=[C:2]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](=[O:33])(=[O:34])[NH2:32])=[CH:27][CH:26]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 67421157HCID 67421157, compound

Product 1

HCID 67421153HCID 67421153, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[Re(CO)3][2-((6-oxo-6-(4-sulfamoylphenylamino)hexyl)(pyridin-2-ylmethyl)amino)acetic acid]. A solution of tert-butyl 2-((6-oxo-6-(4-sulfamoylphenylamino) hexyl)(pyridin-2-ylmethyl)amino)acetate (70 mg, 0.14 mmol) in DCM (1.0 mL) and TFA (1.0 mL) was stirred at room temperature overnight. The solvent was removed under reduced pressure to give 2-((6-oxo-6-(4-sulfamoylphenylamino)hexyl)(pyridin-2-ylmethyl)amino) acetic acid. A solution of the above isolated product, 2-((6-oxo-6-(4-sulfamoylphenylamino) hexyl)(pyridin-2-ylmethyl)amino)acetic acid, [NEt4]2[ReBr3(CO)3] (108 mg, 0.14 mmol) and potassium carbonate (30 mg) in MeOH (4.0 mL) and water (1.0 mL) was stirred at 100° C. for 4 h in a sealed pressure tube. The reaction mixture was purified by Amberchrom™ eluting with MeOH/H2O to give the title compound (64 mg, 65%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.74 (d, J=5.2 Hz, 1H), 8.13 (td, J=7.6, 1.2 Hz, 1H), 7.76-7.55 (m, 5H), 7.56 (t, J=6.4 Hz, 1H), 7.23 (s, 2H), 4.74 (d, J=16.0 Hz, 1H), 4.53 (d, J=16.0 Hz, 1H), 3.82 (d, J=16.8 Hz, 1H), 3.54-3.40 (m, 2H), 3.38 (d, J=16.8 Hz, 1H), 2.38 (t, J=7.4 Hz, 2H), 1.76-1.31 (m, 6H); ESMS m/z: 705.3 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-86dc8c94e6fc4501b6c953ec5d3d0017
Source dataset
uspto-grants-2012_07
Patent number
US08211402B2

Reaction notes

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