Diisopropylethylamine → HCID 178456854, compound

HRID 2039320Notes

Reaction equation

HRID 2039320 reaction equation
[NH2:1][CH:2]([C:5]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13](=[O:21])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH3:22])[N:6]=1)[CH2:3][CH3:4].Br[C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[NH:26][CH:27]=[N:28]2.C(N(C(C)C)CC)(C)C>C(O)CCC>[CH3:22][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[C:13](=[O:21])[N:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:5]([CH:2]([NH:1][C:24]1[N:32]=[CH:31][N:30]=[C:29]3[C:25]=1[N:26]=[CH:27][NH:28]3)[CH2:3][CH3:4])=[N:6]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5287830Purine, 6-bromo-HCID 598410382-(1-amino-propyl)-5-methyl-3-phenyl-3H-quinazolin-4-one

Product 1

HCID 178456854HCID 178456854, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

Compound 17 (100 mg, 0.341 mmol) was combined with 6-bromo purine (75 mg, 0.375 mmol) and diisopropylethylamine (65 uL, 0.375 mmol) in n-butanol (1.0 mL). The reaction was sealed, heated to 120° C., and stirred for 18 hours. The solution was allowed to cool, then concentrated in vacuo. The resulting residue was purified by prep HPLC to provide compound 14 as an olive solid. (ES): m/z 412 (M+H), 206. 1H NMR (300 MHz, DMSO-d6) δ 8.96-9.06 (br. m, 1H), 8.53 (br. s, 1H), 8.51 (s, 1H), 7.68 (t, 1H, J=7.8 Hz), 7.45-7.62 (m, 6H), 7.31 (d, 1H, J=7.3 Hz), 4.76-4.86 (m, 1H), 2.73 (s, 3H), 1.98-2.11 (m, 1H), 1.76-1.94 (m, 1H), 0.79 (t, 3H, J=7.2 Hz). The reaction described above and compound 14 are shown below.

Workup

  1. customThe reaction was sealed
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by prep HPLC

Sources & evidence

ORD record
ord-4f9bd86bbd4a43e0a544ecefcf70fab9
Source dataset
uspto-grants-2013_11
Patent number
USRE044599E1

Reaction notes

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