Trifluoroacetic acid → HCID 66611768, compound

HRID 1621737Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:31]([OH:44])[C:32]4[CH:37]=[CH:36][C:35]([S:38]([N:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])=[CH:34][CH:33]=4)[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[N:10]=2)=CC=1.[C:56]([OH:62])([C:58]([F:61])([F:60])[F:59])=[O:57]>>[F:59][C:58]([F:61])([F:60])[C:56]([OH:62])=[O:57].[NH2:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]2[CH:17]=[C:18]([CH:31]([OH:44])[C:32]3[CH:33]=[CH:34][C:35]([S:38]([N:41]([CH3:42])[CH3:43])(=[O:40])=[O:39])=[CH:36][CH:37]=3)[CH:19]=[N:20][C:21]=2[NH:22][C:23]2[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:10]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 666120144-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide

Product 1

HCID 66611768HCID 66611768, compoundYield 78%

Procedure

A solution of 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide (38.3 mg, 0.050 mmol) in TFA (1.0 mL) was heated at 100° C. in a sealed tube for 5 h. The dark solution was concentrated and purified by prep HPLC to give 4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide trifluoroacetate (25 mg, 0.039 mmol, 78% yield). The sample was recrystallized from dioxane and dried to give a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.79 (s, 1H); 10.37 (br. s., 1H); 9.20 (d, J=2.35 Hz, 1H); 8.60 (d, J=2.54 Hz, 1H); 8.49 (d, J=2.54 Hz, 1H); 8.12 (dd, J=8.80, 2.74 Hz, 1H); 7.85-8.00 (m, 3H); 7.78 (br. s., 1H); 7.56 (td, J=7.58, 1.27 Hz, 1H); 7.35-7.46 (m, 1H); 6.83 (d, J=8.80 Hz, 1H); 6.61 (d, J=9.39 Hz, 1H); 3.84 (s, 3H); 2.84 (d, J=4.50 Hz, 3H); 2.76 (d, J=4.69 Hz, 3H); 2.46 (s, 3H). 19F NMR (376 MHz, d6-DMSO) δ −74.57 (br. s., 3F). m/z (ESI, +ve ion) 523 (M+H)+.

Workup

concentrationThe dark solution was concentrated
custompurified by prep HPLC

Sources & evidence

ORD record: ord-a988c6110bc343a8ae845f5810336925
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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