Benzylamine → HCID 59481191, compound

HRID 560645Notes

Reaction equation

HRID 560645 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.[CH2:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:42]([NH:49][C:19]([C:15]1[S:14][C:13]([N:10]2[CH2:11][CH2:12][N:8]([CH2:1][CH:2]3[CH2:7][CH2:6]3)[C:9]2=[O:22])=[N:17][C:16]=1[CH3:18])=[O:21])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 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 59481191HCID 59481191, compoundYield 26%

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 benzylamine, the title compound was obtained as a white powder in 26% yield: mp 142-143° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.36-7.25 (m, 5H), 5.90 (s, 1H), 4.54 (d, J=5.7 Hz, 2H), 4.09 (t, J=8.4 Hz, 2H), 3.67 (t, J=8.4 Hz, 2H), 3.15 (d, J=7.2 Hz, 2H), 2.60 (s, 3H), 0.97-0.86 (m, 1H), 0.58-0.49 (m, 2H), 0.25-0.19 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 162.4, 157.4, 155.2, 153.0, 137.9, 128.7, 127.8, 127.6, 117.0, 48.6, 44.0, 42.2, 42.1, 17.1, 8.9, 3.4; MS (ES+) m/z 371.1 (M+1).

Sources & evidence

ORD record
ord-23b21d3373c44adeb5b13c083f223437
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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