Dimethylformamide → HCID 59239253, compound

HRID 1698029Notes

Reaction equation

HRID 1698029 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[CH2:29][CH3:30])[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.[CH:36](N(CC)C(C)C)([CH3:38])[CH3:37].C(I)(C)C>>[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[CH2:29][CH3:30])[C:16]3[CH2:22][CH2:21][N:20]([CH:36]([CH3:38])[CH3:37])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 81531DiisopropylethylamineHCID 67178678HCID 67178678, compound

Product 1

HCID 59239253HCID 59239253, compound

Conditions

Temperature
50 °C

Procedure

Step 2—Synthesis of compound xc: (S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.097 g, 0.24 mmol) in dry N,N-Dimethylformamide (1.30 mL, 16.8 mmol) was added N,N-Diisopropylethylamine (0.1270 mL, 0.7291 mmol) followed by Isopropyl iodide (0.0488 mL, 0.488 mmol). The reaction mixture was heated at 50° C. and stirred overnight. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.62 (s, 1H), 8.15 (d, J=8.7, 2H), 7.46 (d, J=8.7, 2H), 6.16 (t, J=5.5, 1H), 3.97 (s, 1H), 3.85 (d, J=10.7, 1H), 3.77 (d, J=11.4, 1H), 3.68 (t, J=13.3, 3H), 3.60-3.49 (m, 2H), 3.40 (t, J=11.0, 1H), 3.18-3.04 (m, 2H), 2.91-2.64 (m, 3H), 2.57 (d, J=15.4, 1H), 1.89-1.63 (m, 2H), 1.06 (t, J=7.5, 9H), 0.94 (t, J=6.3, 1H), 0.82 (t, J=7.4, 3H). LC/MS-m/z+453.2 (M+H)+

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-326bbb4b5ae5419ebe137dcba6c8f551
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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