2-Pyridinemethanamine → HCID 57919942, compound

HRID 554964Notes

Reaction equation

HRID 554964 reaction equation
N1C=CC=C(CN)C=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][NH2:16].FC1C=CC(CN2[C@@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1.[F:41][C:42]1[CH:64]=[CH:63][C:45]([CH2:46][N:47]2[CH2:51][C@H:50]([CH3:52])[N:49]([C:53]3[S:54][C:55]([C:59](O)=[O:60])=[C:56]([CH3:58])[N:57]=3)[C:48]2=[O:62])=[CH:44][CH:43]=1>>[F:41][C:42]1[CH:64]=[CH:63][C:45]([CH2:46][N:47]2[CH2:51][C@H:50]([CH3:52])[N:49]([C:53]3[S:54][C:55]([C:59]([NH:16][CH2:15][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=4)=[O:60])=[C:56]([CH3:58])[N:57]=3)[C:48]2=[O:62])=[CH:44][CH:43]=1

Participants

5

Reactant 4

HCID 195092-PyridinemethanamineHCID 310183-PyridinemethanamineHCID 57919852(S)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57919942HCID 57919942, compound

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with pyridin-2-ylmethanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (S)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid (72%): mp 112-113° C. (diethyl ether/hexane); 1H NMR (300 MHz, DMSO-d6) δ 8.50-8.46 (m, 2H), 7.75-7.70 (m, 1H), 7.34-7.14 (m, 6H), 4.56-4.51 (m, 1H), 4.46-4.39 (m, 4H), 3.56-3.50 (m, 1H), 3.01 (dd, J=9.1, 3.4 Hz, 1H), 2.46 (s, 3H), 1.36 (d, J=6.2 Hz, 3H); MS (ES+) m/z 439.9 (M+1).

Sources & evidence

ORD record
ord-d439069a650243718e9e1e7d9e9abc10
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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