3-Pyridinemethanamine → 5-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

HRID 560728Notes

Reaction equation

HRID 560728 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17]C(C(F)(F)F)=CC=3)[C:8]2=[O:23])[S:4][C:3]=1[C:24]([OH:26])=O.C1(CN2CCN(C3SC(C(O)=O)=C(C)C=3)C2=O)CC1.[NH2:46][CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1>>[CH:13]1([CH2:12][N:9]2[CH2:10][CH2:11][N:7]([C:5]3[S:4][C:3]([C:24]([NH:46][CH2:47][C:48]4[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=4)=[O:26])=[C:2]([CH3:1])[CH:6]=3)[C:8]2=[O:23])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 25095414HCID 25095414, compoundHCID 580315813-Methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid

Product 1

HCID 594811765-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamideYield 59%

Procedure

Following the procedure as described in Example 15, making variations as required to replace 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 59% yield: mp 157-159° C.; 1H NMR (300 MHz, CDCl3) δ 8.51 (s, 1H), 8.50 (d, J=4.1 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.28-7.21 (m, 1H), 6.14 (t, J=5.6 Hz, 1H), 6.06 (s, 1H), 4.57 (d, J=5.6 Hz, 2H), 3.85-3.77 (m, 2H), 3.70-3.63 (m, 2H), 3.14 (d, J=7.1 Hz, 2H), 2.48 (s, 3H), 0.99-0.84 (m, 1H), 0.58-0.50 (m, 2H), 0.25-0.19 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 163.6, 155.8, 149.2, 148.8, 142.8, 141.8, 135.5, 134.2, 123.5, 118.6, 112.1, 48.8, 42.9, 42.1, 41.2, 16.1, 9.0, 3.4; MS (ES+) m/z 371.3 (M+1).

Sources & evidence

ORD record
ord-d7ee35f78f29413aac55f929a80b0b49
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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