Maleic Anhydride → HCID 136347269, compound

HRID 601352Notes

Reaction equation

HRID 601352 reaction equation
[NH2:1][C:2]1[C:11]2[S:10](=[O:13])(=[O:12])[N:9]=[C:8]([C:14]3[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]4[C:22]([C:23]=3[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=4)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:31].[C:32]1(=O)[O:37][C:35](=[O:36])[CH:34]=[CH:33]1>N1C=CC=CC=1>[OH:24][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:15](=[O:30])[C:14]=1[C:8]1[NH:7][C:6]2[CH:5]=[CH:4][C:3]3[O:31][C:32]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[N:1][C:2]=3[C:11]=2[S:10](=[O:12])(=[O:13])[N:9]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 136358419HCID 136358419, compound

Product 1

HCID 136347269HCID 136347269, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the product of Example 354 (15 mg, 0.033 mmol) and maleic anhydride (100 mg, 1.0 mmol) in pyridine (2 mL) was heated at 160° C. in a microwave reactor for 1 hour. The crude mixture was cooled to 25° C. and purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:0.1% aqueous trifluoroacetic to yield the title compound (5.3 mg, 30%). The disodium salt was made by the procedure of Example 1D using 2 equivalents of sodium hydroxide. MS (ESI−) m/z 524 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.03 (d, J=6.25 Hz, 6 H) 1.86 (m, 1 H) 2.27 (m, 4 H) 2.66 (m, 2 H) 5.94 (t, J=7.54 Hz, 1 H) 6.81 (m, 2 H) 7.05 (t, J=7.91 Hz, 1 H) 7.53 (m, 2 H) 8.06 (d, J=6.62 Hz, 1 H) 15.74 (s, 1 H).

Workup

  1. custompurified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-20a1e723c8834dd19f7170da2e933712
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

Loading…