p-Toluenesulfonic acid → HCID 66970672, compound

HRID 1363183Notes

Reaction equation

HRID 1363183 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[N:29]=[C:28]2[C:24]([NH:25][C:26](=[O:41])[N:27]2[C@H:30]2[C:39]3[C:34](=[C:35]([F:40])[CH:36]=[CH:37][CH:38]=3)[O:33][CH2:32][CH2:31]2)=[CH:23][N:22]=1>COC(OC)OC>[F:19][C:17]1[CH:16]=[CH:15][C:14]2[N:20]([C:21]3[N:29]=[C:28]4[C:24]([NH:25][C:26](=[O:41])[N:27]4[C@H:30]4[C:39]5[C:34](=[C:35]([F:40])[CH:36]=[CH:37][CH:38]=5)[O:33][CH2:32][CH2:31]4)=[CH:23][N:22]=3)[CH:1]=[N:12][C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66970457HCID 66970457, compound

Product 1

HCID 66970672HCID 66970672, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

A catalytic amount of p-TsOH was added to a solution of the above amine in trimethylorthoformate (2 mL). The mixture was stirred at RT for 15 hr then the solvents were reduced and the resultant material partitioned between DCM and brine and separated. The crude product was purified via column chromatography (eluted with 5% MeOH/DCM) to yield the titled compound (9 mg). 1H-NMR (300 MHz, CDCl3) δ 10.0 (s, 1H), 8.9 (s, 1H), 8.3 (s, 1H), 7.8 (dd, 1H), 7.4 (d, 1H), 7.1 (m, 2H), 6.8 (m, 2H), 5.9 (dd, 1H), 4.7 (m 1H), 4.4 (td, 1H), 2.9 (m, 1H), 2.4 (m, 1H).

Workup

  1. customthe resultant material partitioned between DCM and brine
  2. customseparated
  3. customThe crude product was purified via column chromatography (eluted with 5% MeOH/DCM)

Sources & evidence

ORD record
ord-aa997670e5494e3a8e626d63061596ee
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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