Diethyl Ether → HCID 86752367, compound

HRID 1597951Notes

Reaction equation

HRID 1597951 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2.Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1.[CH3:27][S:28]([OH:31])(=[O:30])=[O:29].CCOCC>CC(O)C.C(Cl)Cl>[CH3:27][S:28]([OH:31])(=[O:30])=[O:29].[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH3:26])[N:16]=[CH:15][N:14]=[C:13]2[N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 107019745-methoxy-2,3-dihydro-1H-indole

Product 1

HCID 86752367HCID 86752367, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Utilizing a procedure analogous to that described in Example 1, this product was prepared in 95% yield from 5-methoxy-indoline (1.1 eq.), and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. The free-base obtained following column chromatography on silica (45% acetone/hexanes) was dissolved in minimal CH2Cl2 and treated with 1 eq. of methanesulfonic acid in CH2Cl2 followed by dilution with several volumes of ether to precipitate the mesylate salt which was filtered and added in vacuo. (M.P. 285°-292° C. (dec); LC-MS: 338 (MH+); anal. RP18-HPLC RT: 3.82 min.).

Workup

  1. customto precipitate the mesylate salt which
  2. filtrationwas filtered
  3. additionadded in vacuo

Sources & evidence

ORD record
ord-1a0e14bc71f94dad9006bc4b9f293e77
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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