Ethanol → HCID 136079653, compound

HRID 1697989Notes

Reaction equation

HRID 1697989 reaction equation
[CH3:1][N:2]([C:4]([NH:6][C:7](=S)[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]3[CH3:37])[C:18]3[CH2:24][CH2:23][N:22]([C:25]4[N:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:21][C:19]=3[N:20]=2)=[CH:11][CH:10]=1)=[O:5])[NH2:3].C(O)C>>[CH3:1][N:2]1[C:4](=[O:5])[NH:6][C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[C:17]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]4[CH3:37])[C:18]4[CH2:24][CH2:23][N:22]([C:25]5[N:30]=[CH:29][CH:28]=[CH:27][N:26]=5)[CH2:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:3]1

Participants

3

Reactant 2

HCID 702EthanolHCID 86640112HCID 86640112, compound

Product 1

HCID 136079653HCID 136079653, compound

Procedure

Step 3—Synthesis of compound vb: (S)-1-methyl-N-(4-(4-(3-methylmorpholino)-7-(pyrimidin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenylcarbamothioyl)hydrazinecarboxamide (0.113 g, 0.000211 mol) and Ethanol (3.7 mL, 0.063 mol) were combined and the reaction was microwaved on 300 watts, 150° C. for 30 minutes on a CEM microwave. The reaction mixture was chromatographed through silica gel (0-5% MeOH in dichloromethane) and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 9.34 (s, 1H), 8.43 (d, J=4.7, 2H), 8.22 (d, J=8.8, 2H), 7.47 (d, J=8.8, 2H), 6.69 (t, J=4.7, 1H), 4.88 (d, J=18.7, 1H), 4.73 (d, J=18.7, 1H), 4.17-4.04 (m, 2H), 3.91-3.79 (m, 2H), 3.70 (dd, J=11.3, 2.6, 1H), 3.61 (dd, J=9.9, 6.5, 3H), 3.43 (d, J=11.3, 1H), 3.23 (s, 3H), 2.73 (s, 2H), 1.25 (d, J=6.6, 3H). LC/MS-m/z+501.2 (M+H)+

Workup

  1. customthe reaction was microwaved on 300 watts, 150° C. for 30 minutes on a CEM microwave
  2. customThe reaction mixture was chromatographed through silica gel (0-5% MeOH in dichloromethane)
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-252a31549c1d48b6bde148ec498aa0f7
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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