Dimethylformamide → HCID 59239635, compound

HRID 1697997Notes

Reaction equation

HRID 1697997 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.Cl[C:44]([O:46][CH:47]([CH3:49])[CH3:48])=[O:45]>C1(C)C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:5])[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:44]([O:46][CH:47]([CH3:49])[CH3:48])=[O:45])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239635HCID 59239635, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.087 g, 0.23 mmol) in dry N,N-Dimethylformamide (1.00 mL, 12.9 mmol) at 0° C. was added N,N-Diisopropylethylamine (0.1190 mL, 0.6832 mmol) followed by 1.0 M of Isopropyl Chloroformate in Toluene (0.340 mL). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.66 (s, 1H), 8.18 (d, J=8.8, 2H), 7.48 (d, J=8.8, 2H), 6.18 (t, J=5.5, 1H), 4.84 (dt, J=12.5, 6.2, 1H), 4.49 (s, 2H), 3.79-3.68 (m, 4H), 3.55 (s, 2H), 3.47 (d, J=4.4, 4H), 3.18-3.05 (m, 2H), 2.68 (t, J=5.0, 2H), 1.24 (d, J=6.2, 6H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+469.3 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-3695c6d50c354c529ca618aedc053985
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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