Dimethylformamide → HCID 59239649, compound

HRID 1698004Notes

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].CN(C)C=O.C(N(CC)C(C)C)(C)C.[N:43]1[CH:48]=[CH:47][N:46]=[CH:45][C:44]=1[C:49](Cl)=[O:50]>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:16]3[CH2:22][CH2:21][N:20]([C:49]([C:44]4[CH:45]=[N:46][CH:47]=[CH:48][N:43]=4)=[O:50])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 88279Pyrazinecarbonyl chloride

HCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239649HCID 59239649, compound

Conditions

Temperature: 0 °C

Procedure

1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0493 g, 0.000129 mol) in dry N,N-Dimethylformamide (0.610 mL, 0.00788 mol) was added N,N-Diisopropylethylamine (0.0684 mL, 0.000393 mol) cooled at 0° C., added Pyrazine-2-carbonyl chloride (0.0312 g, 0.000219 mol), warmed to room temperature, and stirred overnight. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.98-8.91 (m, 1H), 8.80 (dd, J=5.3, 2.6, 1H), 8.74 (d, J=1.4, 1H), 8.64 (d, J=12.3, 1H), 8.18 (dd, J=34.9, 8.7, 2H), 7.47 (dd, J=20.0, 8.8, 2H), 6.20-6.09 (m, 1H), 4.75 (d, J=25.1, 2H), 3.88 (t, J=5.0, 1H), 3.79-3.60 (m, 5H), 3.49 (d, J=4.0, 4H), 3.18-3.02 (m, 2H), 2.77 (s, 2H), 1.06 (dd, J=13.3, 7.0, 3H). LC/MS-m/z+489.2 (M+H)+.

Workup

temperaturewarmed to room temperature
customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record: ord-758aad61f8004c2cbf0983fafd0f7932
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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