Trifluoroacetic acid → (R)-N-((4-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)pyridin-3-yl)methyl)benzenesulfonamide

HRID 44864Notes

Reaction equation

HRID 44864 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[N:18]=[CH:17][C:16]2[N:15]([CH3:19])[C:14](=[O:20])[C@@H:13]([CH2:21][CH3:22])[N:12]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:11]=2[N:10]=1.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(C(F)(F)F)=O>>[CH:23]1([N:12]2[C:11]3[N:10]=[C:9]([C:8]4[CH:7]=[CH:6][N:5]=[CH:4][C:3]=4[CH2:2][NH:1][S:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:36])=[O:35])[N:18]=[CH:17][C:16]=3[N:15]([CH3:19])[C:14](=[O:20])[C@H:13]2[CH2:21][CH3:22])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7369Benzenesulfonyl chlorideHCID 58405312HCID 58405312, compound

Product 1

HCID 67370909(R)-N-((4-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)pyridin-3-yl)methyl)benzenesulfonamide

Procedure

The title compound was prepared similarly to the methods described in Example 114, with (R)-2-(3-(aminomethyl)pyridin-4-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 105) instead of (R)-2-(3-aminopyridin-4-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 91) and with benzene sulfonylchloride instead of chloromethylcarbonate. LCMS (0.05% TFA): 507.2 m/z (M+H)+; 1H-NMR (MeOD, 500 MHz): δ: 8.82 (s, 1H), 8.76 (bs, 1H), 8.27 (d, 1H, J=5.0 Hz), 8.13 (s, 1H), 7.81 (d, 2H, J=8.0 Hz), 7.62 (t, 1H, J=8 Hz), 7.55 (t, 2H, J=8 Hz), 4.63 (s, 2H), 4.43 (m, 2H), 3.43 (s, 3H), 2.06˜1.65 (m, 10H), 0.88 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record
ord-db6dc41ac10943729b94ed21774d0a54
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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