Butylamine → HCID 15657937, compound

HRID 1655604Notes

Reaction equation

HRID 1655604 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16]>C(O)C>[CH2:13]([NH:17][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 2796614Ethyl chloronicotinate

Product 1

HCID 15657937HCID 15657937, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-chloropyridine-3-carboxylate (8.00 g) was heated at 100° C. for 5 hours with 16 mL of n-butylamine and 34 mL of ethanol in an autoclave. The product was chromatographed on silica gel to give 7.69 g of ethyl 2-butylaminopyridine-3-carboxylate. This compound was reacted with N-triphenylmethyl-5-[2-(4'-bromomethyl-biphenyl)]tetrazole, prepared as described by P. E. Aldrich, et al., in European Patent Application Number 291969, using the procedure described in Example 87 to give ethyl 2-{N-butyl-N-[(2'-[N-triphenylmethyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyridine-3-carboxylate in 61% yield. m.p. 90°-94° C. Treatment of 1.50 g of this compound with 14 mL of methylene chloride and 21 mL of 88% formic acid for 1 hour at ambient temperature gave 690 mg of the title compound. m.p. 120°-121° C. 1H NMR (CDCl3, 300 MHz) d 0.85 (t, J=7 Hz, 3H), 1.22 (m, 2H), 1.36 (t, J=7 Hz, 3H), 1.55 (m, 2H), 3.29 (t, J=7 Hz, 2H), 4.31 (q, J=7 Hz, 2H), 4.60 (s, 2H), 6.69 (dd, J=4 Hz, 8 Hz, 1H), 7.11 (d, J=8 Hz, 2H), 7.25 (d, J=8 Hz, 2H), 7.45 (dd, J=8 Hz, 2 Hz, 1H), 7.50-7.70 (m, 4H), 7.92 (dd, J=8 Hz, 1 Hz, 1H), 8.05 (dd, J=4 Hz, 2 Hz, 1H), 8.17 (dd, J=8 Hz, 1 Hz, 1H).

Workup

  1. customThe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-df7d79653c4d4be8a8d5016e0feecbcc
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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