5-(Aminomethyl)-2-chloropyridine → HCID 25096940, compound

HRID 560895Notes

Reaction equation

HRID 560895 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[F:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41](O)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[Cl:48][C:49]1[N:54]=[CH:53][C:52]([CH2:55][NH2:56])=[CH:51][CH:50]=1>>[Cl:48][C:49]1[N:54]=[CH:53][C:52]([CH2:55][NH:56][C:41]([C:39]2[S:40][C:36]([N:33]3[CH2:34][CH2:35][N:31]([CH2:30][C:29]4[CH:28]=[CH:27][C:26]([F:25])=[CH:47][CH:46]=4)[C:32]3=[O:45])=[CH:37][C:38]=2[CH3:44])=[O:42])=[CH:51][CH:50]=1

Participants

4

Reactant 3

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 25096940HCID 25096940, compoundYield 80%

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-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with (6-chloropyridin-3-yl)methanamine, the title compound was obtained as a colorless solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 8.36 (d, J=1.5 Hz, 1H), 7.68 (dd, J=8.2, 2.4 Hz, 1H), 7.30-7.23 (m, 3H), 7.08-6.99 (m, 2H), 6.13 (t, J=5.8 Hz, 1H), 6.09 (s, 1H), 4.55 (d, J=5.8 Hz, 2H), 4.43 (s, 2H), 3.84-3.76 (m, 2H), 3.48-3.40 (m, 2H), 2.48 (s, 3H); MS (ES+) m/z 459.1 (M+1).

Sources & evidence

ORD record
ord-f2bf054362ca4342b5c70e9cc5b0e134
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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