Trifluoroacetic acid → HCID 67254689, compound

HRID 44863Notes

Reaction equation

HRID 44863 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.[CH3:28][S:29](Cl)(=[O:31])=[O:30].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:29]([CH3:28])(=[O:31])=[O:30])[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 31297Methanesulfonyl chlorideHCID 58405312HCID 58405312, compound

Product 1

HCID 67254689HCID 67254689, compound

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 methane sulfonylchloride instead of chloromethylcarbonate. LCMS (0.05% TFA): 445.2 m/z (M+H)+; 1H-NMR (MeOD, 500 MHz): δ: 8.62 (s, 1H), 8.50 (d, 1H, J=5.0 Hz), 8.05 (s, 1H), 7.82 (d, 1H, J=5.0 Hz), 4.54 (s, 2H), 4.36 (m, 1H), 4.28 (m, 1H), 3.31 (s, 3H), 2.77 (s, 3H), 2.01˜1.58 (m, 10H), 0.78 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record
ord-237a8afbf50f448eac9e29f441dd1eb4
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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