Trifluoroacetic acid → HCID 178434259, compound

HRID 490098Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[C:16]([C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[N:33](CC3C=CC(OC)=CC=3)[N:32]=[C:31]4[CH3:46])[N:17]=[N:18][C:19]=2[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>>[CH3:46][C:31]1[C:30]2[C:34](=[CH:35][CH:36]=[C:28]([C:16]3[N:17]=[N:18][C:19]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[N:15]=3)[CH:29]=2)[NH:33][N:32]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68999522HCID 68999522, compound

Product 1

HCID 178434259HCID 178434259, compoundYield 72.4%

Conditions

Temperature: 120 °C

Procedure

To 5-(4-Boc-piperazin-1-yl)-3-[N-(4-methoxybenzyl)-3-methylindazol-5-yl]-6-phenethyl-[1,2,4]triazine 129 (18 mg, 0.029 mmol.) was added trifluoroacetic acid (2.5 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 40 minutes. Excess trifluoroacetic acid was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 3-(3-methylindazol-5-yl)-6-phenethyl-5-(piperazin-1-yl)-[1,2,4]triazine 92 (8.5 mg, 0.021 mmol.).

Workup

customExcess trifluoroacetic acid was evaporated under reduced pressure
customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-f0638bea811f4168937cdc3749ae39ec
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528132B2

Reaction notes

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