Hydrochloric Acid → HCID 68682547, compound

HRID 2234385Notes

Reaction equation

HRID 2234385 reaction equation
[NH2:1][C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:19])[C:7](=[O:18])[CH2:8][CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.N[C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[O:30][CH2:31][CH3:32].O.Cl>C(O)C>[CH:13]1([N:10]2[CH2:9][CH2:8][C:7](=[O:18])[N:6]([CH3:19])[C:5]3[C:11]2=[N:12][C:2]([NH:1][C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=2[O:30][CH2:31][CH3:32])=[N:3][CH:4]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 223974484-Amino-3-ethoxybenzoic acidHCID 68683478HCID 68683478, compound2×

Product 1

HCID 68682547HCID 68682547, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1; 280 mg, 1 mmol) and 4-amino-3-ethoxybenzoic acid (WO 2001077101; 205 mg, 1.13 mmol) in ethanol (5 mL) was added water (15 mL) and conc hydrochloric acid (0.17 mL, 2 mmol). The mixture was heated under reflux for 36 hours. The reaction was cooled and a brown solid precipitated. This was filtered and dried, triturated under cold acetonitrile and then dried in vacuo. To yield the title compound as a brown solid (190 mg; 45%)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 36 hours
  3. temperatureThe reaction was cooled
  4. customa brown solid precipitated
  5. filtrationThis was filtered
  6. customdried
  7. customtriturated under cold acetonitrile
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1b145ea26eb24d05a22f9533c73962df
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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