Ethyl isothiocyanatoformate → 8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 1889831Notes

Reaction equation

HRID 1889831 reaction equation
BrC1C(N)=NC=C(C(F)(F)F)C=1.C(OC(N=C=S)=O)C.Cl.NO.[Br:24][C:25]1[C:26]2[N:27]([N:35]=[C:36]([NH2:38])[N:37]=2)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.[CH3:39][S:40]([C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1)(=[O:42])=[O:41]>>[Br:24][C:25]1[C:26]2[N:27]([N:35]=[C:36]([NH2:38])[N:37]=2)[CH:28]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:30]=1.[CH3:39][S:40]([C:43]1[CH:48]=[CH:47][C:46]([C:25]2[C:26]3[N:27]([N:35]=[C:36]([NH2:38])[N:37]=3)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=2)=[CH:45][CH:44]=1)(=[O:42])=[O:41]

Participants

7

Reactant 5

HCID 85320Ethyl isothiocyanatoformateHCID 443297Hydroxyamine hydrochlorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amineHCID 674814698-Bromo-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 2

HCID 674814178-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamineHCID 674814698-Bromo-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Procedure

8-Bromo-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 3-bromo-5-trifluoromethyl-pyridin-2-ylamine, ethoxycarbonylisothiocyanate, and hydroxylamine hydrochloride in a manner analogous to Steps 2a-b. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.24 (s, 1H), 8.08 (s, 1H), 6.62 (bs, 2H). MS=282.9 (MH)+. 102b) 8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 8-bromo-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine and (4-methylsulfonylphenyl)boronic acid in a manner analogous to Step 2c to afford a white solid (67%) MP=236-237° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.28 (s, 1H), 8.42 (d, J=7.8 Hz, 2H), 8.07 (s, 1H), 8.06 (d, J=7.8 Hz, 2H), 6.58 (bs, 2H), 3.29 (s, 3H). MS=356.33 (MH)+. 102c) [8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine and 1-(3-bromo-phenyl)-4-methyl-piperazine in a manner analogous to Step 2d and was isolated as a yellow solid (2% yield). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.84 (s, 1H), 8.28 (d, J=8.3 Hz, 2H), 8.14 (d, J=7.2 Hz, 2H), 7.81 (s, 1H), 6.95 (m, 2H), 6.64 (d, 1H), 3.32 (bm, 4H), 3.14 (s, 3H), 2.67 (bm, 4H), 2.44 (s, 3H). MS=531.1 (MH)+.

Sources & evidence

ORD record
ord-f4d3692114ac428f9b8c5737c3052975
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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