Dimethylformamide → HCID 59239353, compound

HRID 1697973Notes

Reaction equation

HRID 1697973 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[CH2:26][CH2:25][NH:24][CH2:23][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17](=[O:22])[CH2:16]4)[N:12]=2)[CH2:3][CH2:2]1.Cl[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[CH2:26][CH2:25][N:24]([C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:23][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17](=[O:22])[CH2:16]4)[N:12]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 67177531HCID 67177531, compound

Product 1

HCID 59239353HCID 59239353, compound

Procedure

Step 3—Synthesis of compound ud: 5-(4-Morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)indolin-2-one (0.083 g, 0.24 mmol), 2-Chloropyrimidine (0.0406 g, 0.354 mmol), N,N-Dimethylformamide (4.00 mL, 51.6 mmol) and N,N-Diisopropylethylamine (0.164 mL, 0.945 mmol) were combined and reaction mixture was microwaved on 300 watts, 120° C. for 30 minutes on a CEM microwave, and vacuum filtered. 1H NMR (400 MHz, DMSO) δ 10.60 (s, 1H), 8.44 (d, J=4.7, 2H), 8.24 (d, J=8.2, 1H), 8.20 (s, 1H), 6.92 (t, J=10.8, 1H), 6.70 (t, J=4.7, 1H), 4.82 (s, 2H), 3.98 (t, J=5.2, 2H), 3.77-3.69 (m, 4H), 3.57 (s, 2H), 3.47 (d, J=4.4, 4H), 2.75 (dd, J=8.8, 3.8, 2H). LC/MS-m/z+430.2 (M+H)+.

Workup

  1. customreaction mixture
  2. customwas microwaved on 300 watts, 120° C. for 30 minutes on a CEM microwave, and vacuum
  3. filtrationfiltered

Sources & evidence

ORD record
ord-7d0b95c3c33e469bb6195070b053617a
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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