Diisopropylethylamine → HCID 57794717, compound

HRID 2099837Notes

Reaction equation

HRID 2099837 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.Cl.[NH:39]1[CH2:44][CH2:43][CH:42]([C:45]2[C:46](=[O:55])[NH:47][C:48]3[C:53]([CH:54]=2)=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:41][CH2:40]1.C(N(C(C)C)CC)(C)C>>[O:55]=[C:46]1[C:45]([CH:42]2[CH2:43][CH2:44][N:39]([C:1]([O:2][C@H:3]([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]([CH3:21])([CH3:22])[CH3:20])[N:10]=4)[CH:6]=3)[C:23]([O:25][CH3:26])=[O:24])=[O:27])[CH2:40][CH2:41]2)=[CH:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[NH:47]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 577946441-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonateHCID 673176623-piperidin-4-yl-1H-quinolin-2-one;hydrochloride

Product 1

HCID 57794717HCID 57794717, compoundYield 30%

Procedure

To a solution of 1-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonate (0.859 mmol) was added 3-(piperidin-4-yl)quinolin-2(1H)-one-hydrochloride (682 mg, 2.58 mmol), in one portion, followed by dropwise addition of diisopropylethylamine (0.37 mL, 2.15 mmol) at room temperature. The resulting yellow suspension was stirred at room temperature overnight. The mixture was extracted with ethyl acetate (2×2 mL) and the organic phase was washed with brine and dried over sodium sulfate. The crude product was purified using preparative HPLC to afford (R)-1-methoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (157 mg, 30%). Mass spec. 619.24 (MH+). 1H-NMR (CDCl3, 400 MHz) δ 8.0 (s, 1H), 7.53 (br s, 2H), 7.47-7.43 (m, 1H), 7.34-7.31 (m, 1H), 7.21-7.18 (m, 1H), 6.96 (s, 1H), 5.7 (s, 2H), 5.23 (dd, J=8.6, 4.6 Hz, 1H), 4.28 (br s, 2H), 3.74 (s, 3H), 3.61 (m, 2H), 3.13 (m, 3H), 2.93 (m, 2H), 2.59 (s, 3H), 1.94 (m, 2H), 0.92 (m, 2H), −0.064 (s, 9H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×2 mL)
  2. washthe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-97b7baeb212f40fb8f952c762c8b6dfb
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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