Trifluoroacetic acid → HCID 68328950, compound

HRID 634162Notes

Reaction equation

COC1C=CC(C[NH:8][C:9]2[S:10][C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][CH:18]=[C:17]4[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N:29]4[CH2:34][CH2:33][N:32]5[C:35]([CH3:38])=[N:36][N:37]=[C:31]5[CH2:30]4)[N:24]=3)=[N:12][N:13]=2)=CC=1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>>[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42].[CH3:38][C:35]1[N:32]2[CH2:33][CH2:34][N:29]([C:25]3[N:24]=[C:23]([C:17]4[C:16]5[C:20](=[CH:21][CH:22]=[C:14]([C:11]6[S:10][C:9]([NH2:8])=[N:13][N:12]=6)[CH:15]=5)[NH:19][CH:18]=4)[CH:28]=[CH:27][CH:26]=3)[CH2:30][C:31]2=[N:37][N:36]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68328363HCID 68328363, compound

Product 1

HCID 68328950HCID 68328950, compoundYield 2.5%

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with N-(4-methoxybenzyl)-5-(3-(6-(3-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (80.0 mg, 0.146 mmol) in TFA (1.0 mL). The reaction was heated in a microwave at 100° C. for 10 min, then solvent was removed. The residue was purified with RP-HPLC to give 5-(3-(6-(3-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine 2,2,2-trifluoroacetate (2.0 mg, 2.5%) as a light yellow solid. MS (ESI, pos. ion) m/z: 430 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.73 (1H, br. s.), 8.80 (1H, s), 8.14 (1H, d, J=2.0 Hz), 7.61-7.72 (2H, m), 7.52 (1H, d, J=8.6 Hz), 7.22-7.43 (3H, m), 6.90 (1H, d, J=9.2 Hz), 5.07 (2H, br. s.), 4.15-4.37 (4H, m).

Workup

customA glass microwave reaction vessel
customsolvent was removed
customThe residue was purified with RP-HPLC

Sources & evidence

ORD record: ord-b6c85c057e77444fb5d6102b093daee5
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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