Diisopropylethylamine → HCID 59239614, compound

HRID 1697968Notes

Reaction equation

HRID 1697968 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.Cl.[CH2:7]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:22]3[CH2:28][CH2:27][NH:26][CH:25]([CH3:29])[C:23]=3[N:24]=2)=[CH:15][CH:14]=1)=[O:11])[CH3:8].C(N(CC)C(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:7]([NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[C:22]3[CH2:28][CH2:27][N:26]([CH:3]4[CH2:2][O:1][CH2:4]4)[CH:25]([CH3:29])[C:23]=3[N:24]=2)=[CH:17][CH:18]=1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 67176741HCID 67176741, compound

Product 1

HCID 59239614HCID 59239614, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

3-oxetanone (0.38 mL, 5.2 mmol) and 1-ethyl-3-(4-(8-methyl-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride salt (451 mg, 1.04 mmol) were mixed in 1,2-Dichloroethane (6.2 mL) and N,N-Diisopropylethylamine (0.73 mL, 4.2 mmol). The reaction was stirred at 70° C. for 1 h and at 80° C. for 30 minutes. Sodium triacetoxyborohydride (0.71 g, 3.3 mmol) was added to the reaction, and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was quenched with NaHCO3 and water, which was extracted by CHCl3. The organic layers were combined, washed by water and brine (final pH ˜9), dried over Magnesium sulfate and evaporated. The residue was purified to give the desired product sk (269 mg, 57% yield) as white powder: 1H NMR (400 MHz, DMSO) δ 8.62 (s, 1H), 8.18 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 6.14 (t, J=5.5 Hz, 1H), 4.62 (m, 3H), 4.53 (t, J=6.2 Hz, 1H), 4.04 (p, J=6.7 Hz, 1H), 3.81-3.64 (m, 5H), 3.54-3.35 (m, 4H), 3.17-3.03 (m, 2H), 2.67 (m, 4H), 1.29 (d, J=6.8 Hz, 3H), 1.06 (t, J=7.2 Hz, 3H); LC-MS m/z=453 (M+H).

Workup

  1. stirringthe mixture was stirred at 80° C. for 30 minutes
  2. customThe reaction mixture was quenched with NaHCO3 and water, which
  3. extractionwas extracted by CHCl3
  4. washwashed by water and brine (final pH ˜9),
  5. dry with materialdried over Magnesium sulfate
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-3254ac502e29486b8dfbb27a0150c02d
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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