Dimethylformamide → HCID 66916321, compound

HRID 2054149Notes

Reaction equation

HRID 2054149 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:25][CH3:26].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:33][CH:34](OS([C:40]1[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=1)(=O)=O)[CH3:35].C[N:48](C=O)C>>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][N:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:35][CH2:34][Cl:33])=[C:3]([O:25][CH3:26])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:22])([CH3:23])[CH3:24].[CH3:26][O:25][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:42][CH2:41][CH:40]1[CH2:46][CH2:45][CH2:43][CH2:44][NH:48]1)[N:9]=[CH:8][N:7]=[C:6]2[N:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 21956426HCID 21956426, compoundHCID 135545160HCID 135545160, compound

Product 2

HCID 22260370HCID 22260370, compoundHCID 66916321HCID 66916321, compoundYield 40%

Procedure

To the DMF solution (10 mL) of tert-butyl 4-(7-hydroxy-6-methoxyquinazolin-4-yl)piperazinecarboxylate (1.88 g, 5 mmol), Cs2CO3 (3.3 g, 10 mmol) added 1-chloroethyl-tosylate (1.8 mL, 10 mmol). The mixture was stirred overnight at room temperature. The solvent was evaporated and the crude residue was purified by RP-HPLC to afford the intermediate tert-butyl-4-[6-methoxy-7-(2-chloroethoxy)quinazolin-4-yl]piperazinecarboxylate as the desired product (850 mg, 40%). MS(ES) 423 (M+H)

Workup

  1. customThe solvent was evaporated
  2. customthe crude residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-0054219531f04ba0901ed4bc9d6a8595
Source dataset
uspto-grants-2008_02
Patent number
US07329655B2

Reaction notes

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