4-(Morpholin-4-yl)benzoic acid → HCID 69214290, compound

HRID 2218416Notes

Reaction equation

HRID 2218416 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[CH:4][N:3]=1.[N:11]1([C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=O)=[CH:19][CH:18]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>O=P(Cl)(Cl)Cl>[Cl:10][C:5]1[C:6]([Cl:9])=[C:7]2[NH:8][C:21]([C:20]3[CH:19]=[CH:18][C:17]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[CH:25][CH:24]=3)=[N:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 3452784-(Morpholin-4-yl)benzoic acidHCID 454802354,5-Dichloropyridine-2,3-diamine

Product 1

HCID 69214290HCID 69214290, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
105 °C

Procedure

2,3-Diamino-4,5-dichloropyridine (Example 206a) (0.10 g, 0.56 mmol) and 4-morpholin-4-ylbenzoic acid (0.12 g, 0.56 mmol) were dissolved in POCl3 (5 ml) and heated to 105° C. for 5 h. The excess of POCl3 was evaporated off and the residue was dissolved in EtOAc and aqueous K2CO3. The aqueous phase was extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), evaporated in vacuo and the residue was purified by HPLC-C18. The product crystallized from the chromatography fraction and was filtered off and dried to yield a white powder (0.040 g, 20%).

Workup

  1. customThe excess of POCl3 was evaporated off
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionThe aqueous phase was extracted three times with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customthe residue was purified by HPLC-C18
  8. customThe product crystallized from the chromatography fraction
  9. filtrationwas filtered off
  10. customdried

Sources & evidence

ORD record
ord-ecc2ecbb8ebf4e43829bdacf0534195e
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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