p-Toluenesulfonic acid → HCID 136373882, compound

HRID 601346Notes

Reaction equation

HRID 601346 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].[CH:32](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[O:13]=[S:10]1(=[O:12])[C:11]2[C:2]3[N:1]=[CH:32][O:31][C:3]=3[CH:4]=[CH:5][C:6]=2[NH:7][C:8]([C:14]2[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]3[C:22]([C:23]=2[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:9]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 136358419HCID 136358419, compound

Product 1

HCID 136373882HCID 136373882, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 354 (0.036 g, 0.081 mmol) in dimethylformamide (2 mL) was treated with trimethyl orthoformate (1 mL) and a catalytic amount of para-toluenesulfonic acid at room temperature for 20 hours. The solvent was removed under a stream of warm nitrogen and the residue was triturated with 1:1 ethyl acetate: tetrahydrofuran, filtered, and dried to yield the title compound (8 mg, 22%). MS (ESI−) m/z 452 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.05 (d, J=6.62 Hz, 6 H) 1.93 (m, 1 H) 2.78 (m, 2 H) 6.33 (m, 1 H) 7.45 (t, J=7.54 Hz, 1 H) 7.73 (d, J=8.82 Hz, 1 H) 7.92 (t, J=7.72 Hz, 1 H) 8.00 (m, 1 H) 8.21 (m, 2 H) 9.04 (s, 1 H) 14.28 (s, 1 H).

Workup

  1. customThe solvent was removed under a stream of warm nitrogen
  2. customthe residue was triturated with 1:1 ethyl acetate
  3. filtrationtetrahydrofuran, filtered
  4. customdried

Sources & evidence

ORD record
ord-1df66ef8e2f44584bdcd74bc7fe2160c
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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