Dimethylformamide → HCID 59239524, compound

HRID 1698017Notes

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][C@@H:24]3[CH3:29])[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:44]1[CH:49]=[CH:48][N:47]=[CH:46][C:45]=1[C:50](Cl)=[O:51]>>[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[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH3:29])[C:16]3[CH2:22][CH2:21][N:20]([C:50]([C:45]4[CH:46]=[N:47][CH:48]=[CH:49][N:44]=4)=[O:51])[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 46913570Urea, N-ethyl-N'-[4-[5,6,7,8-tetrahydro-4-[(3S)-3-Methyl-4-Morpholinyl]pyrido[3,4-d]pyriMidin-2-yl]phenyl]-

Product 1

HCID 59239524HCID 59239524, compound

Conditions

Temperature: 0 °C

Procedure

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.085 g, 0.00021 mol) in dry N,N-Dimethylformamide (1.00 mL, 0.0129 mol) was added N,N-Diisopropylethylamine (0.1120 mL, 0.0006430 mol) cooled at 0° C., added Pyrazine-2-carbonyl chloride (0.0508 g, 0.000356 mol) stirred at 0° C. for 30 minutes. The reaction mixture was filtered and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.95 (dd, J=8.4, 1.3, 1H), 8.81 (dd, J=7.1, 2.5, 1H), 8.75 (d, J=3.9, 1H), 8.68 (d, J=15.6, 1H), 8.17 (dd, J=43.7, 8.7, 2H), 7.48 (dd, J=25.1, 8.8, 2H), 6.18 (dt, J=11.1, 5.6, 1H), 4.85 (d, J=18.5, 1H), 4.72 (d, J=7.4, 1H), 4.11 (d, J=5.5, 1H), 3.88 (d, J=9.3, 1H), 3.78-3.54 (m, 6H), 3.43 (t, J=12.3, 1H), 3.11 (dq, J=14.5, 7.2, 2H), 2.76 (s, 2H), 1.26 (d, J=6.6, 3H), 1.06 (q, J=7.3, 3H). LC/MS-m/z+503.2 (M+H)+.

Workup

filtrationThe reaction mixture was filtered
custompurified by HPLC

Sources & evidence

ORD record: ord-b58edee3023e419188baada4ba291451
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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