Water → HCID 68060885, compound

HRID 1520061Notes

Reaction equation

HRID 1520061 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:13](=O)[CH2:14][C:15]2[CH:16]=[C:17]([N:21]3[CH:25]=[C:24]([C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[NH:28][N:27]=4)[N:23]=[N:22]3)[CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.O.CCOC(C)=O>C1COCC1>[N:7]1([CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([N:21]3[CH:25]=[C:24]([C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[NH:28][N:27]=4)[N:23]=[N:22]3)[CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 68060988HCID 68060988, compound

Product 1

HCID 68060885HCID 68060885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (1M in THF, 107 μl; 0.26 mmol; 2.0 eq.) was added dropwise to a cooled (0° C.) solution of 3-{1-[3-(2-morpholin-4-yl-2-oxoethyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazole (50 mg, 0.13 mmol, 1 eq.) in dry THF (1 mL). The reaction mixture was allowed to warm to RT and stirred overnight. Water was added and the reaction mixture was extrated three times with EtOAc. Combined organic phases were dried over magnesium sulfate, filtered and concentratd. The crude was purified by preparative HPLC to give the title compound as a beige powder. 1H NMR (300 MHz, DMSO-d6) δ 13.37 (brs, 1H), 9.31 (s, 1H), 8.37 (dt, J=8.2 Hz, 1.0 Hz, 1H), 7.96 (t, J=1.5 Hz, 1H), 7.90-7.87 (m, 1H), 7.61 (dt, J=1.0, 8.4 Hz, 1H), 7.53 (t, J=7.9 Hz, 1H), 7.47-7.41 (m, 1H), 7.40-7.38 (m, 1H), 7.28-7.23 (m, 1H), 3.59 (t, J=4.6 Hz, 4H), 2.91-2.86 (m, 2H), 2.64-2.59 (m, 2H), 2.47 (t, J=4.6 Hz, 4H). HPLC (Condition A): Rt 2.47 min (purity 95.5%). MS (ESI+): 375.2, MS (ESI−): 373.3.

Workup

  1. dry with materialCombined organic phases were dried over magnesium sulfate
  2. filtrationfiltered
  3. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-214a746b6a5e421d891add94e4421a2a
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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