Dibutyltin dichloride → [8-(3-Chloro-4-fluoro-phenyl)-6-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(6-methyl-pyrimidin-4-yl)-piperidin-4-yl]-amine

HRID 451454Notes

Reaction equation

C([Sn](Cl)(Cl)CCCC)CCC.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[C:21]3[N:22]([N:29]=[C:30]([NH2:32])[N:31]=3)[CH:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[CH:25]=2)[CH:16]=[CH:17][C:18]=1[F:19].[CH3:33][C:34]1[N:39]=[CH:38][N:37]=[C:36]([N:40]2[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]2)[CH:35]=1.C1([SiH3])C=CC=CC=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[C:21]3[N:22]([N:29]=[C:30]([NH:32][CH:43]4[CH2:44][CH2:45][N:40]([C:36]5[CH:35]=[C:34]([CH3:33])[N:39]=[CH:38][N:37]=5)[CH2:41][CH2:42]4)[N:31]=3)[CH:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[CH:25]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of dibutyl tin chloride (10 mg, 0.03 mmol) and 8-(3-chloro-4-fluoro-phenyl)-6-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (prepared in analogy to example 48a-e, 100 mg, 0.33 mmol) in dry THF (1.5 mL) were added 1-(6-methyl-pyrimidin-4-yl)-piperidin-4-one (example 93b, 63 mg, 0.33 mmol) and phenyl silane (0.016 mL, 0.4 mmol) under an argon atmosphere and heated to 100° C. in the microwave for 40 minutes. The reaction mixture was cooled to room temperature, the solvent was evaporated and the residue was purified by prep-HPLC (acetonitrile/H2O). The title compound was obtained as a white solid (20 mg, 13%). MS ESI (m/z): 477.8 [(M+H)+].

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated
customthe residue was purified by prep-HPLC (acetonitrile/H2O)

Sources & evidence

ORD record: ord-76ae6e40999b46dca2006527308a3861
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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