Ethanol → HCID 59239603, compound

HRID 1697978Notes

Reaction equation

HRID 1697978 reaction equation
C([O:3][C:4]1[C:5](=[O:39])[C:6](=O)[C:7]=1[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)C.Cl.[CH2:41]([NH2:43])[CH3:42].C(O)C.C(N(CC)CC)C>>[CH2:41]([NH:43][CH:6]1[CH: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)[C:4](=[O:3])[C:5]1=[O:39])[CH3:42]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 86640108HCID 86640108, compound

Product 1

HCID 59239603HCID 59239603, compound

Procedure

Step 2—Synthesis of compound un: (S)-3-ethoxy-4-(4-(4-(3-methylmorpholino)-7-(pyrimidin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenylamino)cyclobut-3-ene-1,2-dione (0.087 g, 0.00016 mol), Ethylamine Hydrochloride (0.0780 g, 0.000956 mol), and Ethanol (8.00 mL, 0.137 mol) were combined then added Triethylamine (0.230 mL, 0.00165 mol) and stirred overnight. The reaction mixture was concentrated, and chromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane). 1H NMR (400 MHz, DMSO) δ 9.83 (s, 1H), 8.44 (d, J=4.7, 2H), 8.31 (d, J=8.7, 2H), 7.72 (s, 1H), 7.53 (d, J=8.5, 2H), 6.69 (t, J=4.7, 1H), 4.90 (d, J=18.7, 1H), 4.75 (d, J=18.6, 1H), 4.14 (t, J=9.3, 2H), 3.85 (dd, J=20.6, 7.2, 2H), 3.74-3.55 (m, 6H), 3.44 (t, J=11.9, 1H), 2.75 (s, 2H), 1.31-1.15 (m, 6H). LC/MS-m/z+527.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-a06c733bdd994ce5951577f976ee9855
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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