Trimethylamine → HCID 86708107, compound

HRID 1497796Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:41])[NH:7][C:8]1[N:40]=[C:11]2[C:12]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)=[C:13]([CH3:29])[C:14]([C:16]3[N:17]([C:21]4[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=4)[N:18]=[CH:19][CH:20]=3)=[CH:15][N:10]2[N:9]=1.[CH3:42][N:43]([CH3:45])[CH3:44]>CC#N.CCO>[Cl-:1].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([N:17]2[C:16]([C:14]3[C:13]([CH3:29])=[C:12]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=4)[C:11]4[N:10]([N:9]=[C:8]([NH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][N+:43]([CH3:45])([CH3:44])[CH3:42])=[O:41])[N:40]=4)[CH:15]=3)=[CH:20][CH:19]=[N:18]2)=[CH:22][CH:23]=1)#[N:28]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of [6-[2-(4-cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-carbamic acid 3-chloro-propyl ester (Int. 20, 125 mg, 0.218 mmol) in MeCN (3.5 mL) was treated with trimethylamine solution in EtOH (4.2M, 1.5 mL) and heated for 1 hr at 100° C. using microwave irradiation. A further amount of trimethylamine in EtOH was added (1 mL) and the heating continued at 100° C. for 20 mins. The reaction mixture was concentrated in vacuo then azeotroped with toluene in vacuo. The resultant residue was subjected to preparative C18 HPLC chromatography, eluting with a gradient of 10-70% MeCN in water+0.1% formic acid) to give the title compound as a white solid (20 mg).

Workup

custommicrowave irradiation
concentrationThe reaction mixture was concentrated in vacuo
customthen azeotroped with toluene in vacuo
washeluting with a gradient of 10-70% MeCN in water+0.1% formic acid)

Sources & evidence

ORD record: ord-697a4b417f26420ebadd0e32cd794d4c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199984B2

Reaction notes

Loading…