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

HRID 44868Notes

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

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 31297Methanesulfonyl chloride

HCID 58405371HCID 58405371, compound

Product 1

HCID 67373085(R)-N-((4-(7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)pyridin-3-yl)methyl)methanesulfonamide

Procedure

The title compound was prepared similarly to the methods described in Example 114, with (R)-2-(3-(aminomethyl)pyridin-4-yl)-7-ethyl-8-isopropyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 126) instead of (R)-2-(3-aminopyridin-4-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 91) and with methane sulfonylchloride instead of chloromethylcarbonate. LCMS (0.05% TFA): 419.2 m/z (M+H)+; 1H-NMR (DMSO-d6, 500 MHz): δ: 8.87 (s, 1H), 8.81 (d, 1H, J=5.0 Hz), 8.27 (d, 1H, J=5.0 Hz), 8.22 (s, 1H), 4.75 (d, 2H, J=5.0 Hz), 4.60 (m, 1H), 4.44 (m, 1H), 3.33 (s, 3H), 2.93 (s, 3H), 1.84 (m, 1H), 1.73 (m, 1H), 1.36 (t, 6H, J=7.5 Hz), 0.76 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record: ord-85eb5fbd6a574872a69f762d317fa166
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Reaction notes

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