3-Pyridinemethanamine → HCID 57919960, compound

HRID 554963Notes

Reaction equation

HRID 554963 reaction equation
N1C=CC=C(CN)C=1.[CH3:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][NH2:16])[CH:11]=1.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:43]=[C:44]([CH:62]=[C:63]([F:65])[CH:64]=1)[CH2:45][N:46]1[C@H:50]([CH3:51])[CH2:49][N:48]([C:52]2[S:53][C:54]([C:58](O)=[O:59])=[C:55]([CH3:57])[N:56]=2)[C:47]1=[O:61]>>[F:65][C:63]1[CH:62]=[C:44]([CH:43]=[C:42]([F:41])[CH:64]=1)[CH2:45][N:46]1[C@H:50]([CH3:51])[CH2:49][N:48]([C:52]2[S:53][C:54]([C:58]([NH:16][CH2:15][C:12]3[CH:11]=[C:10]([CH3:9])[O:14][N:13]=3)=[O:59])=[C:55]([CH3:57])[N:56]=2)[C:47]1=[O:61]

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 66661653HCID 66661653, compound

Product 1

HCID 57919960HCID 57919960, compound

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with (5-methylisoxazol-3-yl)methanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid: mp 63-66° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 8.50 (t, J=5.4 Hz, 1H), 7.17-7.08 (m, 3H), 6.14 (s, 1H), 4.57 (d, J=16.2 Hz, 1H), 4.42-4.36 (m, 3H), 4.25-4.21 (m, 1H), 3.88-3.81 (m, 1H), 3.62-3.57 (m, 1H), 2.48 (s, 3H), 2.37 (s, 3H), 1.23 (d, J=5.9 Hz, 3H); MS (ES+) m/z 462.0 (M+1).

Sources & evidence

ORD record
ord-f464ba52f2914d078392122e18ac7f78
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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