Methanol → HCID 59239063, compound

HRID 1697994Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

Step 2—Synthesis of vg: (S)-1-(4-(7-(4-chloro-1,3,5-triazin-2-yl)-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (0.147 g, 0.000288 mol), Palladium on Carbon 10% (0.1:0.9, Palladium:carbon black, 0.116 g), and Methanol (10.0 mL, 0.247 mol) were combined under N2 then purged with hydrogen, heated at 65° C. and stirred overnight. The reaction mixture was purged with N2, added celite, filtered through celite, filtered through a disc filter, concentrated, and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.71 (s, 1H), 8.67 (d, J=2.0, 2H), 8.20 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.21 (t, J=5.6, 1H), 4.91 (d, J=18.6, 1H), 4.77 (d, J=18.6, 1H), 4.20-4.02 (m, 2H), 3.87 (d, J=12.5, 2H), 3.69 (d, J=8.4, 1H), 3.66-3.56 (m, 3H), 3.47-3.36 (m, 1H), 3.17-3.06 (m, 2H), 2.76 (s, 2H), 1.25 (d, J=6.7, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+476.2 (M+H)+.

Workup

customthen purged with hydrogen
customThe reaction mixture was purged with N2
additionadded celite
filtrationfiltered through celite
filtrationfiltered through a disc
filtrationfilter
concentrationconcentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-ed2ea75e8cec4d378c4a8cc250ded5a5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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