Dimethylformamide → 1-Ethyl-3-(4-(7-(3-methylpyrazine-2-carbonyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1698020Notes

Reaction equation

HRID 1698020 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.CN(C)C=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:47]([NH:49][C:50]([NH:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[N:60]=[C:61]([N:69]3[CH2:74][CH2:73][O:72][CH2:71][CH2:70]3)[C:62]3[CH2:68][CH2:67][NH:66][CH2:65][C:63]=3[N:64]=2)=[CH:55][CH:54]=1)=[O:51])[CH3:48]>>[CH2:47]([NH:49][C:50]([NH:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]2[N:60]=[C:61]([N:69]3[CH2:70][CH2:71][O:72][CH2:73][CH2:74]3)[C:62]3[CH2:68][CH2:67][N:66]([C:8]([C:3]4[C:2]([CH3:1])=[N:7][CH:6]=[CH:5][N:4]=4)=[O:10])[CH2:65][C:63]=3[N:64]=2)=[CH:57][CH:58]=1)=[O:51])[CH3:48]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131534683-Methylpyrazine-2-carboxylic acidHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 592395221-Ethyl-3-(4-(7-(3-methylpyrazine-2-carbonyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

Procedure

3-Methylpyrazine-2-carboxylic acid (0.0501 g, 0.000363 mol) in dry N,N-Dimethylformamide (1.80 mL, 0.0232 mol) was added 1-Hydroxybenzotriazole (0.0580 g, 0.000429 mol) followed by N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0765 g, 0.000399 mol) then followed by N,N-Diisopropylethylamine (0.1150 mL, 0.0006602 mol) and then 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.1021 g, 0.0002670 mol). The reaction mixture was stirred overnight. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.73-8.60 (m, 2H), 8.55 (s, 1H), 8.17 (dd, J=43.9, 8.8, 2H), 7.47 (dd, J=25.7, 8.8, 2H), 6.22-6.10 (m, 1H), 4.79 (s, 1H), 4.37 (s, 1H), 3.90 (t, J=5.3, 1H), 3.78-3.66 (m, 4H), 3.56-3.37 (m, 6H), 3.21-3.03 (m, 2H), 2.81 (s, 1H), 2.68 (s, 1H), 2.53 (s, 2H), 1.06 (q, J=7.3, 3H). LC/MS-m/z+503.2 (M+H)+

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-eca343df635a4994b8fd77fa42b80963
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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