2-(Aminomethyl)-5-methylpyrazine → HCID 59481225, compound

HRID 560665Notes

Reaction equation

HRID 560665 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6]C=CC=1.C1(CN2CCN(C3SC(C(O)=O)=C(C)N=3)C2=O)CC1.[NH2:42][CH2:43][C:44]1[CH:49]=[N:48][C:47]([CH3:50])=[CH:46][N:45]=1>>[CH:2]1([CH2:1][N:8]2[CH2:12][CH2:11][N:10]([C:13]3[S:14][C:15]([C:19]([NH:42][CH2:43][C:44]4[CH:49]=[N:48][C:47]([CH3:50])=[CH:46][N:45]=4)=[O:21])=[C:16]([CH3:18])[N:17]=3)[C:9]2=[O:22])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 59481225HCID 59481225, compoundYield 43%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-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 2-(aminomethyl)-5-methylpyrazine, the title compound was obtained as a white powder in 43% yield: mp 161-163° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.46 (s, 1H), 8.33 (s, 1H), 6.77 (t, J=4.8 Hz, 1H), 4.64 (d, J=4.8 Hz, 2H), 4.09-4.01 (m, 2H), 3.68-3.58 (m, 2H), 3.14 (d, J=7.2 Hz, 2H), 2.57 (s, 3H), 2.50 (s, 3H), 0.96-0.85 (m, 1H), 0.55-0.49 (m, 2H), 0.23-0.18 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.7, 157.7, 155.2, 153.1, 152.5, 148.8, 143.4, 142.7, 117.2, 48.6, 42.3, 42.2, 42.1, 21.2, 17.3, 8.9, 3.5; MS (ES+) m/z 387.2 (M+1).

Sources & evidence

ORD record
ord-b39d9e80a7dc4c85a0f3e2694859b39a
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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