Hydrochloric Acid → HCID 18932860, compound

HRID 1597964Notes

Reaction equation

HRID 1597964 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.O.O.O.O.O.[OH-].C[N+](C)(C)C.Br[CH2:34][CH2:35][CH2:36][OH:37].Cl>CN(C=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:34][CH2:35][CH2:36][OH:37])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 123083-Bromo-1-propanol2×HCID 82620Tetramethylammonium Hydroxide PentahydrateHCID 136119078HCID 136119078, compound

Product 1

HCID 18932860HCID 18932860, compoundYield 144.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 4-(6-chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-ol (125 mg, 0.42 mmol; from Example 65) in DMF (2 mL) was added H2O (50 μL), K2 CO3 (s) (116 mg, 0.84 mmol) and tetramethylammonium hydroxide pentahydrate (15 mg, 0.08 mmol) followed by 3-bromopropanol (43 μL, 0.46 mmol). The mixture was stirred at 50° C. under N2(g) for 24 hours before another aliquot (11 μL) of 3-bromopropanol was added. After heating another 24 hours, extractive workup and chromatography analogous to that described in Example 1 followed by conversion to the HCl salt as outlined for Example 2 afforded 119 mg (70%) of product. (M.P. 211°-223° C. (dec); LC-MS: 356 (MH+); anal. RP18-HPLC RT: 4.40 min.; M.P. of free-base: 137°-138° C.).

Workup

  1. additionwas added
  2. temperatureAfter heating another 24 hours

Sources & evidence

ORD record
ord-fa05caaa7895467e829c5bf3254455b6
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…