3-Pyridinemethanamine → HCID 25097714, compound

HRID 560843Notes

Reaction equation

HRID 560843 reaction equation
ClC1C=CC2S[CH:7]=[C:8]([CH2:9][N:10]3[CH2:14][CH2:13][N:12]([C:15]4[S:16][C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[N:19]=4)[C:11]3=[O:24])[C:4]=2C=1.[CH:27]1([CH2:30][N:31]2[CH2:35][CH2:34][N:33](C3SC(C(O)=O)=C(C)N=3)C2=O)[CH2:29][CH2:28]1.N1C=CC=C(CN)C=1>>[CH:8]1([CH2:9][N:10]2[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([C:21]([NH:33][CH2:34][C:35]4[CH:29]=[CH:28][CH:27]=[CH:30][N:31]=4)=[O:23])=[C:18]([CH3:20])[N:19]=3)[C:11]2=[O:24])[CH2:7][CH2:4]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 25097714HCID 25097714, compoundYield 64%

Procedure

Following the procedure as described in Example 32, making variations as required to replace 2-(3-((5-chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a colorless solid in 64% yield: mp 148-151° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.54 (d, J=4.9 Hz, 1H), 7.70-7.64 (m, 1H), 7.31-7.23 (m, 1H), 7.21-7.18 (m, 1H), 7.11-7.09 (m, 1H), 4.69 (d, J=4.9 Hz, 2H), 4.15-4.09 (m, 2H), 3.73-3.67 (m, 2H), 3.19 (d, J=7.1 Hz, 2H), 2.64 (s, 3H), 1.00-0.91 (m, 1H), 0.60-0.54 (m, 2H), 0.27-0.22 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.8, 155.9, 155.2, 152.4, 148.8, 136.8, 122.4, 122.0, 117.8, 48.6, 44.6, 42.3, 42.1, 17.2, 8.9, 3.4; MS (ES+) m/z 372.3 (M+1).

Sources & evidence

ORD record
ord-c7a9a7199a32463cbb392f0fa4cb0c39
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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