4-[2-(Morpholin-4-yl)ethoxy]benzoic acid → HCID 178478272, compound

HRID 2218380Notes

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][O: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]([O: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

Conditions

Temperature: 100 °C

Procedure

2,3-Diamino-4,5-dichloropyridine (Example 206a) (0.50 g, 2.5 mmol) and 4-(2-morpholin-4-ylethoxy)benzoic acid (Example 206c) (0.80 g, 2.5 mmol) were dissolved in POCl3 (10 ml) and heated to 100° C. for 10 h. The excess of POCl3 was evaporated off and the residue was dissolved in EtOAc and aqueous NaHCO3. The aqueous phase was basified with 10M NaOH and extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated in vacuo to afford the title product as a slightly yellow powder (0.74 g, 75%).

Workup

customThe excess of POCl3 was evaporated off
dissolutionthe residue was dissolved in EtOAc
extractionextracted three times with EtOAc
washThe combined organic phases were washed with brine
dry with materialdried (Na2SO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-8d1bbbcbe301406193523e4e3c3d4f2f
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410966B2

Reaction notes

Loading…