Water → N-(2-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-ethyl)-3-methyl-butyramide

HRID 472736Notes

Reaction equation

HRID 472736 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:22][C:23]([NH:25][C:26]2[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:27]=2[O:35][CH3:36])=[O:24])[C:12]1=[O:37].[C:38](Cl)(=[O:43])[CH2:39][CH:40]([CH3:42])[CH3:41].O>C1COCC1.C(N(CC)CC)C>[Cl:32][C:30]1[C:29]([O:33][CH3:34])=[CH:28][C:27]([O:35][CH3:36])=[C:26]([NH:25][C:23]([CH2:22][N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:21])[N:11]([CH2:10][CH2:9][NH:8][C:38](=[O:43])[CH2:39][CH:40]([CH3:42])[CH3:41])[C:12]2=[O:37])=[O:24])[CH:31]=1

Participants

6

Reactant 3

HCID 962WaterHCID 66054Isovaleryl chlorideHCID 685885032-[3-(2-Amino-ethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide trifluoroacetate

Product 1

HCID 59317713N-(2-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-ethyl)-3-methyl-butyramide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 2-[3-(2-amino-ethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide trifluoroacetate (75 mg, 0.17 mmol) in THF (1 ml), triethylamine is added (0.06 ml, 0.43 mmol) followed by isovaleryl chloride (30 mg, 0.26 mmol). The mixture is stirred overnight at RT and then treated with water (3 ml). The resulting solid is filtered and washed with water to afford the title compound; [M+H]+ 517.3.

Workup

  1. additionis added (0.06 ml, 0.43 mmol)
  2. filtrationThe resulting solid is filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-230534be6159401087b6977478e26c8c
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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