Pyridine → HCID 44816974, compound

HRID 1697976Notes

Reaction equation

HRID 1697976 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]4[CH3:32])[C:19]4[CH2:25][CH2:24][NH:23][CH2:22][C:20]=4[N:21]=3)=[CH:12][CH:11]=2)[NH:4][C:3]1=[O:33].CN(C)C=O.N1C=CC=CC=1.[S:45]1[CH:49]=[CH:48][N:47]=[C:46]1[C:50](Cl)=[O:51]>>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]4[CH3:32])[C:19]4[CH2:25][CH2:24][N:23]([C:50]([C:46]5[S:45][CH:49]=[CH:48][N:47]=5)=[O:51])[CH2:22][C:20]=4[N:21]=3)=[CH:12][CH:11]=2)[NH:4][C:3]1=[O:33]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 27952111,3-Thiazole-2-carbonyl chlorideHCID 59239640HCID 59239640, compound

Product 1

HCID 44816974HCID 44816974, compound

Procedure

(S)-3-methyl-6-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenylamino)pyrimidine-2,4(1H,3H)-dione (0.0325 g, 0.0000723 mol) in dry N,N-Dimethylformamide (2.00 mL, 0.0258 mol) was added dry Pyridine (0.030 mL, 0.00037 mol) followed by 1,3-thiazole-2-carbonyl chloride (0.0300 g, 0.000203 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated, chromatographed through silica gel (4 g, 0-10% MeOH in dichloromethane), and then purifed by HPLC. 1H NMR (400 MHz, DMSO) δ 10.74 (s, 1H), 8.69 (s, 1H), 8.32 (t, J=7.8, 2H), 8.13-8.04 (m, 2H), 7.31 (dd, J=8.3, 4.7, 2H), 5.50 (dd, J=75.0, 18.3, 1H), 5.04 (d, J=2.8, 1H), 4.79 (dd, J=47.1, 18.7, 1H), 4.67-4.28 (m, 1H), 4.17 (d, J=6.1, 1H), 4.05-3.73 (m, 2H), 3.73-3.55 (m, 4H), 3.45 (dd, J=17.5, 7.1, 1H), 3.09 (s, 3H), 2.82 (d, J=22.7, 2H), 1.28 (d, J=6.7, 3H). LC/MS-m/z+561.2 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed through silica gel (4 g, 0-10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-8cde1090c0634be6b8473ccc065f0776
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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