p-Toluenesulfonic acid monohydrate → HCID 58923368, compound

HRID 1951053Notes

Reaction equation

HRID 1951053 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([OH:14])[CH:10]=[C:11](O)[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[C:16]1[CH:17]=[CH:18][C:19](S(O)(=O)=O)=[CH:20][CH:21]=1.O.CO[C:29](=[O:40])[C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]=1[NH2:39]>C(O)CCCCC>[CH2:18]([O:36][C:34]([C:33]1[CH:37]=[CH:38][C:30]2[C:29](=[O:40])[C:10]3[C:11]([NH:39][C:31]=2[CH:32]=1)=[CH:12][C:7]([N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)=[CH:8][C:9]=3[OH:14])=[O:35])[CH2:17][CH2:16][CH2:21][CH2:20][CH3:19]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acidHCID 58923367HCID 58923367, compound

Product 1

HCID 58923368HCID 58923368, compound

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

5-Morpholin-4-yl-benzene-1,3-diol (290 mg, 1.50 mmol), TsOH.H2O (30 mg, 0.20 mmol), and 2-amino-terephthalic acid 1-methyl ester (290 mg, 1.50 mmol) were heated at 160° C. in hexanol (5 mL) for 12 hours. The reaction mixture was cooled to room temperature. A red/orange precipitate was filtered, and the solid washed with EtOAc/hexanes (3:1, 30 mL) to yield 159 mg (31%). 1H NMR (CDCl3, 400 MHz) δ: 13.90 (s, 1H), 11.9 (s, 1H), 8.22 (d, 1H), 8.07 (s, 1H), 7.68 (d, 1H), 6.27 (s, 1H), 6.19 (s, 1H), 4.33 (t, 2H), 3.74-3.64 (m, 4H), 3.33-3.22 (m, 4H), 1.76-1.73 (m, 2H), 1.54-1.20 (m, 6H), 0.89 (5, 3H). LRMS (APCI, positive): Da/e 425.2 (m+1).

Workup

  1. filtrationA red/orange precipitate was filtered
  2. washthe solid washed with EtOAc/hexanes (3:1, 30 mL)
  3. customto yield 159 mg (31%)

Sources & evidence

ORD record
ord-956c6044a2b54e2d83bab9ba0723a691
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

Loading…