Dimethylformamide → HCID 67176627, compound

HRID 1698000Notes

Reaction equation

HRID 1698000 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].Cl[C:30]1[N:35]=[C:34]([C:36]#[N:37])[CH:33]=[N:32][CH:31]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[C:36]([C:34]1[N:35]=[C:30]([N:20]2[CH2:21][CH2:22][C:16]3[C:15]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:14][C:13]([C:10]4[CH:9]=[CH:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:11]=4)=[N:18][C:17]=3[CH2:19]2)[CH:31]=[N:32][CH:33]=1)#[N:37]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 813036-Chloropyrazine-2-carbonitrileHCID 81531DiisopropylethylamineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 67176627HCID 67176627, compound

Procedure

1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0513 g, 0.134 mmol) and 6-chloropyrazine-2-carbonitrile (0.0326 g, 0.234 mmol) were combined then added dry N,N-Dimethylformamide (0.910 mL, 11.8 mmol) followed by N,N-Diisopropylethylamine (0.0456 mL, 0.262 mmol). The reaction was microwaved on 300 watts, 120° C. for 30 minutes on the Biotage microwave. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.76 (s, 1H), 8.66 (s, 1H), 8.35 (s, 1H), 8.22 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.18 (t, J=5.5, 1H), 4.75 (s, 2H), 3.90 (t, J=5.3, 2H), 3.74 (d, J=4.4, 4H), 3.50 (d, J=4.3, 4H), 3.17-3.06 (m, 2H), 2.81 (s, 2H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+486.2 (M+H)+

Workup

  1. customThe reaction was microwaved on 300 watts, 120° C. for 30 minutes on the Biotage microwave
  2. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-3ffebb3a5c75410cbf561c9601f338ef
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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