Pyridine → HCID 131718369, compound

HRID 487883Notes

Reaction equation

HRID 487883 reaction equation
CC([N:5]([C:11](=[O:17])[NH:12][O:13][CH2:14][CH2:15][Cl:16])[CH2:6][CH2:7][C:8](Cl)=[O:9])CC.O=S(Cl)Cl.[CH:22]([NH2:26])([CH2:24][CH3:25])[CH3:23].N1C=CC=CC=1.C(=O)=O.CC(C)=O>C(Cl)(Cl)Cl>[CH3:23][CH:22]([NH:26][C:8](=[O:9])[CH2:7][CH2:6][NH:5][C:11](=[O:17])[NH:12][O:13][CH2:14][CH2:15][Cl:16])[CH2:24][CH3:25]

Participants

7

Reactant 5

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 24874Sec-ButylamineHCID 18522661Acetone cardiceHCID 19091404HCID 19091404, compound

Product 1

HCID 131718369HCID 131718369, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of N-(1-methylpropyl)-β-chloroethoxycarbamyl-β-alaninyl chloride [prepared from 9.8 g (0.05 mol) of 7 and 10 mL of SOCl2 as described earlier]in 20 ML of CHCl3 was added to a solution of 4 g (0.055 mol) of sec-butylamine and 4.4 g (0.055 mol) of pyridine in 50 mL of CHCl3 at dry ice-acetone temperature. After 16 h the reaction mixture was worked up as described earlier to give 7.05 g (58%) of 51: mp 97°-98° C.; 1H NMR (CDCl3) δ 0.89 (t, 3, CH2CH3), 1.12 (d, 3, CHCH3), 1.45 (m, 2, CH2CH3) 2.40 (t, 2, CH2CO) , 3.46 (m, 2, NCH2) , 3.65 (t, 2, CH2Cl), 3.92 (m, 1, NHCH--) and 4.29 (t, 2, --CH2OCO).

Sources & evidence

ORD record
ord-f83f409e49984570a1be2bd0b04eb058
Source dataset
uspto-grants-1994_03
Patent number
US05298499

Reaction notes

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