Dimethylformamide → HCID 59239434, compound

HRID 1698010Notes

Reaction equation

HRID 1698010 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.C(Cl)Cl.CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH2:25]([NH:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:38]=[C:39]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)[C:40]3[CH2:46][CH2:45][NH:44][CH2:43][C:41]=3[N:42]=2)=[CH:33][CH:32]=1)=[O:29])[CH3:26].C(N(CC)C(C)C)(C)C>>[Cl:1][C:2]1[C:3]([C:8]([N:44]2[CH2:45][CH2:46][C:40]3[C:39]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[N:38][C:37]([C:34]4[CH:33]=[CH:32][C:31]([NH:30][C:28]([NH:27][CH2:25][CH3:26])=[O:29])=[CH:36][CH:35]=4)=[N:42][C:41]=3[CH2:43]2)=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 6

HCID 6228Dimethylformamide2×HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 15019003-Chloro-2-pyrazine-carboxylic acidHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239434HCID 59239434, compound

Procedure

3-Chloropyrazine-2-carboxylic acid (0.0648 g, 0.000409 mol) in dry Methylene chloride (1.50 mL, 0.0234 mol) was added N,N-Dimethylformamide (0.00200 mL, 0.0000258 mol) followed by Oxalyl chloride (0.040 mL, 0.00047 mol) dropwise. The reaction mixture was stirred for 3 hours then concentrated, added 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.102 g, 0.000267 mol), N,N-Dimethylformamide (1.80 mL, 0.0232 mol), and N,N-Diisopropylethylamine (0.180 mL, 0.00103 mol) and stirred overnight. The reaction mixture was filtered and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.76 (dd, J=5.6, 2.5, 1H), 8.70-8.60 (m, 2H), 8.17 (dd, J=39.6, 8.8, 2H), 7.47 (dd, J=23.6, 8.8, 2H), 6.17 (dd, J=13.2, 5.7, 1H), 4.79 (s, 1H), 4.42 (s, 1H), 3.91 (t, J=5.4, 1H), 3.80-3.66 (m, 4H), 3.54-3.41 (m, 5H), 3.19-3.05 (m, 2H), 2.81 (t, J=5.1, 1H), 2.69 (t, J=5.0, 1H), 1.06 (q, J=7.2, 3H). LC/MS-m/z+523.2 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. stirringstirred overnight
  3. filtrationThe reaction mixture was filtered
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-e85bc0b4f3024da3819e949e5e631f42
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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