Triethylamine → 5-({2-Fluoro-5-methoxy-3-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]methyl)-2-pyrimidin-2-yl-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1161526Notes

Reaction equation

[NH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].C(N(CC)CC)C.C[O:17][C:18](=O)[N:19]=[C:20](SC)[C:21]([C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[C:37]([O:43][CH2:44][CH2:45][O:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[C:36]=1[F:53])=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[C:32]([CH3:34])[O:31][N:30]=2)=[CH:25][CH:24]=1>CN(C=O)C>[F:53][C:36]1[C:37]([O:43][CH2:44][CH2:45][O:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:35]=1[C:21](=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[C:32]([CH3:34])[O:31][N:30]=2)=[CH:25][CH:24]=1)[C:20]1[NH:19][C:18](=[O:17])[N:1]([C:3]2[N:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[N:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

After adding 13 mg of 2-hydrazinopyrimidine and 0.016 ml of triethylamine to a solution of 69 mg of (2-{2-fluoro-5-methoxy-3-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester in 1 ml of DMF, the mixture was stirred at 85° C. for 16 hours under a nitrogen atmosphere. The reaction mixture was concentrated to give a crude product of 5-({2-fluoro-5-methoxy-3-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]methyl)-2-pyrimidin-2-yl-2,4-dihydro-[1,2,4]triazol-3-one.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-2e7064fd31e94ec59da51420c0d5514d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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