Dimethylformamide → HCID 59239155, compound

HRID 1697971Notes

Reaction equation

HRID 1697971 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.C[N:10]([CH3:13])[CH:11]=[O:12].O[N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.Cl.CN(C)[CH2:27][CH2:28][CH2:29]N=C=NCC.[CH:36](N(CC)C(C)C)(C)C.C(NC(NC1C=CC(C2N=[C:59]([N:67]3[CH2:72][CH2:71][O:70][CH2:69][CH2:68]3)[C:60]3[CH2:66][CH2:65][NH:64][CH2:63][C:61]=3N=2)=CC=1)=O)C>>[CH2:13]([NH:10][C:11]([NH:15][C:19]1[CH:20]=[CH:21][C:22]([C:28]2[CH:29]=[C:61]3[C:60]([CH2:66][CH2:65][N:64]([C:6]([C:4]4[N:3]=[CH:2][O:1][CH:5]=4)=[O:8])[CH2:63]3)=[C:59]([N:67]3[CH2:68][CH2:69][O:70][CH2:71][CH2:72]3)[CH:27]=2)=[CH:23][CH:18]=1)=[O:12])[CH3:36]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 142814301,3-Oxazole-4-carboxylic acidHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239155HCID 59239155, compound

Procedure

To (Oxazole-4-carboxylic acid (0.0106 g, 0.0000937 mol) in dry N,N-Dimethylformamide (0.460 mL, 0.00594 mol) was added 1-Hydroxybenzotriazole (0.0125 g, 0.0000925 mol) followed by N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0184 g, 0.0000960 mol) then followed by N,N-Diisopropylethylamine (0.0286 mL, 0.000164 mol) and then followed by 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0242 g, 0.0000633 mol). The reaction mixture was stirred overnight. The reaction solution was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.71 (d, J=14.3, 2H), 8.59 (d, J=1.0, 1H), 8.20 (t, J=9.1, 2H), 7.49 (d, J=7.4, 2H), 6.22 (t, J=5.5, 1H), 5.10 (s, 1H), 4.70 (s, 1H), 4.08 (s, 1H), 3.81 (s, 1H), 3.73 (d, J=4.3, 4H), 3.49 (d, J=4.3, 4H), 3.18-3.05 (m, 2H), 2.77 (d, J=26.3, 2H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+478.2 (M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-164f076f6752429291c7cade9f5f2bc1
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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