Pyridine → HCID 10052502, compound

HRID 1684104Notes

Reaction equation

HRID 1684104 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([NH2:20])=[C:7]([O:18][CH3:19])[C:8]([C:14](=[O:17])[NH:15][CH3:16])=[C:9]([NH2:13])[C:10]=1[O:11][CH3:12])=[O:4].N1[CH:26]=[CH:25]C=CC=1.[Br:27][CH2:28][C:29](Cl)=[O:30].[K+].[Br-:33].CN(C)C=[O:37]>C(O)CCC.C(O)(=O)C.O>[Br:33][CH2:25][C:26]([NH:13][C:9]1[C:8]([C:14](=[O:17])[NH:15][CH3:16])=[C:7]([O:18][CH3:19])[C:6]([NH:20][C:29](=[O:30])[CH2:28][Br:27])=[C:5]([C:3](=[O:4])[NH:2][CH3:1])[C:10]=1[O:11][CH3:12])=[O:37]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 89602Bromoacetyl chlorideHCID 253877Potassium BromideHCID 9970997HCID 9970997, compound

Product 1

HCID 10052502HCID 10052502, compound

Reagents, catalysts & solvents 1

HCID 22056973Butanol acetic acid waterSolvent

Procedure

To a solution of 503 mg (1.42 mmol) of 9 .2HCl in 15 mL of dry dimethyl formamide were added sequentially, 533 μL (6.59 mmol) of pyridine and 282 μL (3.42 mmol) of bromoacetyl chloride. After allowing the mixture to stir at room temperature for 6 hours, the precipitated product was filtered off and rinsed with water and then rinsed with ethanol: 393 mg (53%) yield; mp 308°-310° C.; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.58; IR (KBr pellet) 3380, 3278, 1681, 1638, 1551, 1472, 1411, 1325, 1238, 1047 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ9.72 (2H, s, 2- and 5-acetamido N(H), 7.87 (2H, brs, 3- and 6-carbamyl proton), 4.22 (4H, s, methylenes), 3.65 (6H, s, methoxys), 2.70 (6H, d, J=4.6 Hz, 3- and 6-carbamyl methyl); mass spectrum (EI mode) m/z 522, 524 and 526 (P+ for the 79Br, 79Br; 79Br, 81Br; 81Br, 81Br combinations, respectively, at an intensity ratio of 1:2:1).

Workup

  1. filtrationthe precipitated product was filtered off
  2. washrinsed with water
  3. washrinsed with ethanol
  4. custom393 mg (53%) yield

Sources & evidence

ORD record
ord-9034fde3a9164a89af163dfcf8e9706e
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

Loading…