3-Pyridinemethanamine → HCID 59481222, compound

HRID 560882Notes

Reaction equation

HRID 560882 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:54]=[CH:53][C:36]([CH2:37][N:38]2[CH2:42][CH2:41][N:40]([C:43]3[S:47][C:46]([C:48](O)=[O:49])=[C:45]([CH3:51])[CH:44]=3)[C:39]2=[O:52])=[CH:35][CH:34]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[NH2:55][CH2:56][C:57]1[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=1>>[CH3:51][C:45]1[CH:44]=[C:43]([N:40]2[CH2:41][CH2:42][N:38]([CH2:37][C:36]3[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:27])([CH3:28])[CH3:26])=[CH:54][CH:53]=3)[C:39]2=[O:52])[S:47][C:46]=1[C:48](=[O:49])[NH:55][CH2:56][C:57]1[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580316425-(3-(4-(Tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 59481222HCID 59481222, compoundYield 75%

Procedure

Following the procedures as described in Example 55, making variations as required to replace 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-(4-(tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a beige solid in 75% yield: 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.53 (d, J=4.5 Hz, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.33 (d, J=8.3 Hz, 2H), 7.27 (dd, J=7.8, 4.5 Hz, 1H), 7.21 (d, J=8.3 Hz, 2H), 6.51 (br s, 1H), 6.08 (br s, 2H), 4.58 (d, J=5.8 Hz, 2H), 4.40 (s, 2H), 3.82-3.73 (m, 2H), 3.45-3.37 (m, 2 H), 2.50 (s, 3H), 1.51 (s, 9H); MS (ES+) m/z 522.5 (M+1).

Sources & evidence

ORD record
ord-f5637ec2372741b281d997a8feac477e
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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