p-Toluenesulfonic acid → HCID 136347266, compound

HRID 601347Notes

Reaction equation

HRID 601347 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].[Cl:32][CH2:33][C:34](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[Cl:32][CH2:33][C:34]1[O:31][C:3]2[CH:4]=[CH:5][C:6]3[NH:7][C:8]([C:14]4[C:15](=[O:30])[N:16]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]5[C:22]([C:23]=4[OH:24])=[CH:21][CH:20]=[CH:19][CH:18]=5)=[N:9][S:10](=[O:12])(=[O:13])[C:11]=3[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 136358419HCID 136358419, compound

Product 1

HCID 136347266HCID 136347266, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 354 (0.030 g, 0.067 mmol) in dimethylformamide (3 mL) was treated with 2-chloro-1,1,1-trimeth oxyethane (0.50 mL) and a catalytic amount of para-toluenesulfonic acid at 60° C. for 4 hours. The solvent was removed under a stream of warm nitrogen and the resulting residue was triturated with water and filtered, then triturated with methanol and filtered to yield the title compound (22 mg, 51%). The sodium salt was made by the procedure of Example 1D. MS (ESI−) m/z 500 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.04 (d, J=6.62 Hz, 6 H) 1.87 (m, J=20.04, 13.42, 6.99 Hz, 1 H) 2.63 (m, 2 H) 5.13 (s, 2 H) 5.95 (t, J=6.99 Hz, 1 H) 7.08 (t, J=7.54 Hz, 1 H) 7.36 (d, J=9.19 Hz, 1 H) 7.57 (m, 2 H) 7.99 (d, J=8.82 Hz, 1 H) 8.09 (dd, J=7.91, 1.29 Hz, 1 H) 16.59 (s, 1 H).

Workup

  1. customThe solvent was removed under a stream of warm nitrogen
  2. customthe resulting residue was triturated with water
  3. filtrationfiltered
  4. customtriturated with methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-cc40c8f13db24e27865398dc2618cd76
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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