Trifluoroacetic acid → HCID 58405832, compound

HRID 44867Notes

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.[C:26](O)([C:28](F)(F)F)=[O:27]>>[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][C:26](=[O:27])[C:28]3[CH:6]=[CH:7][CH:8]=[CH:3][CH:2]=3)[N:18]=[CH:17][C:16]=2[N:15]([CH3:19])[C:14]1=[O:20])[CH3:22]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58405371HCID 58405371, compound

Product 1

HCID 58405832HCID 58405832, compound

Procedure

The title compound was prepared similarly to the methods described in Example 102, 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). LCMS (0.05% TFA): 445.2 m/z (M+H)+; 1H-NMR (MeOD, 500 MHz): δ: 8.89 (bs, 1H), 8.82 (bs, 1H), 8.43 (d, 1H, J=5.0 Hz), 8.24 (s, 1H), 7.80 (d, 2H, J=7.5 Hz), 7.57 (t, 1H, J=7.5 Hz), 7.47 (t, 2H, J=7.5 Hz), 5.12 (d, 2H, J=6 Hz), 4.73 (m, 1H), 4.49 (m, 1H), 3.42 (s, 3H), 1.99 (m, 1H), 1.81 (m, 1H), 1.46 (t, 6H, J=7.5 Hz), 0.87 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record: ord-a1571728537e42fe854b64acbfa987a9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541418B2

Reaction notes

Loading…