Diisopropylethylamine → HCID 57794647, compound

HRID 2099836Notes

Reaction equation

HRID 2099836 reaction equation
[C:1](=O)([O:27]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH:3]([C:23]([O:25][CH3:26])=[O:24])[CH2:4][C:5]1[CH:13]=[C:12]([CH3:14])[C:11]2[C:7](=[CH:8][N:9]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=2)[CH:6]=1.[NH:38]1[CH2:43][CH2:42][CH:41]([N:44]2[CH2:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[NH:46][C:45]2=[O:54])[CH2:40][CH2:39]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[O:54]=[C:45]1[N:44]([CH:41]2[CH2:42][CH2:43][N:38]([C:1]([O:2][CH:3]([C:23]([O:25][CH3:26])=[O:24])[CH2:4][C:5]3[CH:13]=[C:12]([CH3:14])[C:11]4[C:7](=[CH:8][N:9]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=4)[CH:6]=3)=[O:27])[CH2:39][CH2:40]2)[CH2:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 577946441-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonate

Product 1

HCID 57794647HCID 57794647, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask was charged with 1-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonate (27 mg, 51 mmoles) and 3,4-dihydro-3-(piperidin-4-yl)quinazolin-2(1H)-one (34 mg, 2.8 equiv). The solids were dissolved in dimethylformamide (1 mL) and treated with diisopropylethylamine (0.1 mL, 11 equiv). The reaction was stirred at room temperature for 2 d. The reaction was concentrated, dissolved in ethyl acetate, washed with 20% potassium hydroxide (3×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (100% ethyl acetate) removed baseline material to give 50 mg (quant.). Mass spec.: 622.50 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with 20% potassium hydroxide (3×)
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography (100% ethyl acetate) removed baseline material
  7. customto give 50 mg (quant.)

Sources & evidence

ORD record
ord-6a1c28a3ffae46778888f5ca486c11b0
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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