2,5-Dichloropyridine-3-carboxylic acid → Methyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

HRID 1293189Notes

Reaction equation

HRID 1293189 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[NH2:13][C@H:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)[CH3:15]>>[Cl:1][C:2]1[C:3]([C:4]([NH:13][C@H:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH3:15])=[O:6])=[CH:7][C:8]([Cl:11])=[CH:9][N:10]=1

Participants

3

Reactant 2

HCID 27360852,5-Dichloropyridine-3-carboxylic acidHCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride

Product 1

HCID 86601543Methyl 4-((1S)-1-{[(2,5-dichloropyridin-3-yl)carbonyl]amino}ethyl)benzoate

Procedure

The title compound was prepared according to the procedure described in step 1 of Example 45 from 2,5-dichloronicotinic acid and methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 5): 1H-NMR (CDCl3) δ 8.42 (1H, d, J=2.6 Hz), 8.10 (1H, d, J=2.6 Hz), 8.04 (2H, d, J=8.6 Hz), 7.46 (2H, d, J=8.6 Hz), 6.82 (1H, d, J=7.3 Hz), 5.40–5.30 (1H, m), 3.92 (3H, s), 1.64 (3H, d, J=7.0 Hz); MS (ESI) m/z 353 (M+H)+, 351 (M−H)−.

Sources & evidence

ORD record
ord-e079aadef3b04e2ba897b0b3d0656efe
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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