Sulfuric Acid → HCID 59454966, compound

HRID 1400517Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:15]3[CH:16]=[N:17][CH:18]=[N:19][CH:20]=3)(O)[CH3:13])[C:6]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[OH-].[K+]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](/[C:15]3[CH:16]=[N:17][CH:18]=[N:19][CH:20]=3)\[CH3:13])[C:6]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 14797Potassium Hydroxide

HCID 57876112HCID 57876112, compound

Product 1

HCID 59454966HCID 59454966, compound

Procedure

1-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-2-(pyrimidin-5-yl)propan-2-ol (1 g, 2.80 mmol, 1 eq.) was refluxed with 25% sulfuric acid (7 ml) for 2 h. The reaction mixture was cooled to 5 deg C. in ice-water bath. KOH (15% aqueous solution) was added dropwise to the reaction mixture till pH of 9-10 was achieved. The reaction mixture was extracted with EtOAc (3×10 mL). The combined organic layer was washed with water (10 ml) followed by brine, dried over sodium sulfate and evaporated under vacuum. The crude product was purified by silica gel chromatography (100-200 mesh) using a gradient of MeOH-EtOAc (0-10%) followed by preparative HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 9.20 (s, 1H), 9.10 (s, 2H), 7.58 (s, 1H), 7.30-7.20 (m, 3H), 4.78 (m, 1H), 4.40 (m, 1H), 3.90 (m, 1H), 3.60 (m, 1H), 3.20 (m, 2H), 3.10 (s, 3H), 2.0 (s, 3H).

Workup

temperatureThe reaction mixture was cooled to 5 deg C
extractionThe reaction mixture was extracted with EtOAc (3×10 mL)
washThe combined organic layer was washed with water (10 ml)
dry with materialdried over sodium sulfate
customevaporated under vacuum
customThe crude product was purified by silica gel chromatography (100-200 mesh)

Sources & evidence

ORD record: ord-fab734b0c2114bffadde85c6fe87cd53
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

Loading…