HCID 17965030, compound → HCID 178478270, compound

HRID 2218420Notes

Reaction equation

HRID 2218420 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([CH2:17][CH2:18][NH:19][C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=O)=[CH:22][CH:21]=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[N:8]=[C:24]([C:23]3[CH:27]=[CH:28][C:20]([NH:19][CH2:18][CH2:17][N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[CH:21][CH:22]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 17965030HCID 17965030, compoundHCID 454802354,5-Dichloropyridine-2,3-diamine

Product 1

HCID 178478270HCID 178478270, compoundYield 2%

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-[(2-morpholin-4-ylethyl)amino]benzoic acid (prepared in a manner analogous to Example 206c) (0.14 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, giving the title product (0.006 g, 2%).

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

Sources & evidence

ORD record
ord-af2d72afb08e45a1bc3a08215492e239
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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