Aluminium lithium hydride → HCID 178505446, compound

HRID 1956373Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18](=O)[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:14][CH2:13]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOC(C)=O.[OH-].[Na+]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][N:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:16][CH2:17]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 6-fluoro-3-[4-(2-phenylacetyl)piperazin-1-ylmethyl]-1H-indazole (156 mg, 0.44 mmol) in THF (5 mL) was treated with LiAlH4 (0.44 mL of a 1.0M solution in THF, 0.44 mmol) and heated at 40° C. for 16 h. The solution was cooled, diluted with EtOAc (50 mL), 2M aqueous NaOH was added (200 mL) and the resulting suspension was stirred for 1 h at 20° C., filtered, concentrated and the residue purified by flash chromatography (EtOAc→10% MeOH in EtOAc) to give the title compound (130 mg, 87%) as a white solid; mp 148°-149° C. (from Et2O/hexane); 1H NMR (360 MHz, d6 -DMSO) δ12.85 (bs, 1H, NH), 7.89 (dd, J=8.9, 5.5 Hz, 1H, indazole), 7.28-7.14 (m, 6H, aromatic), 6.96 (dt, J=9.3, 2.2 Hz, 1H, indazole), 3.79 (s, 2H, Ar--CH2N), 2.70 (t, J=7.2 Hz, 2H, CH2 --Ph), 2.51-2.40 (m, 10H, piperazine, CH2); MS (CI+) m/e 339 (M+H+); Anal. calcd for C20H23FN4 : C, 70.98; H, 6.85, N, 16.56. Found: C, 71.35; H, 6.88; N, 16.56.

Workup

temperatureThe solution was cooled
additionwas added (200 mL)
filtrationfiltered
concentrationconcentrated
customthe residue purified by flash chromatography (EtOAc→10% MeOH in EtOAc)

Sources & evidence

ORD record: ord-f5722870194449d8bb28ce453a4e9f1a
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780475

Reaction notes

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