(2-Oxopyrrolidin-1-yl)acetaldehyde → Ethyl 5-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethyl]amino}pyridine-2-carboxylate

HRID 2364140Notes

Reaction equation

HRID 2364140 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH:8]=O.[NH2:10][C:11]1[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:13][CH:14]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:16]=1>>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C:15]2[CH:16]=[C:11]([NH:10][CH2:8][CH2:7][N:3]3[CH2:4][CH2:5][CH2:6][C:2]3=[O:1])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:13][CH:14]=2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 22405515(2-Oxopyrrolidin-1-yl)acetaldehydeHCID 42637772Ethyl 3-amino-5-(4-fluorobenzyl)picolinate

Product 1

HCID 58882948Ethyl 5-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethyl]amino}pyridine-2-carboxylate

Procedure

(2-Oxopyrrolidin-1-yl)acetaldehyde and ethyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate were treated in a manner similar to that described in Example 5, Step 1 to yield the product as an amber oil: 1H NMR (CDCl3) δ 7.89 (1H, d, J=1.4 Hz), 7.83 (1H, br t, J˜6 Hz), 7.15 (2H, dd, J˜9, 6 Hz), 6.98 (2H, t, J˜9 Hz), 6.92 (1H, s), 4.42 (2H, q, J=7 Hz), 3.92 (2H, s), 3.49 (2H, m), 3.41 (2H, t, J=7 Hz), 3.35 (2H, q, J=6 Hz), 2.36 (2H, t, J=8 Hz), 1.99 (2H, m), 1.42 (3H, t, J=7 Hz); HRMS calcd for C21H24FN3O3+H+: 386.1880. Found: 386.1880.

Sources & evidence

ORD record
ord-5f4b2072b5fb4c58bcfc56b8e9186221
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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