Pyridine → Phenyl 4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-ylcarbamate

HRID 1968652Notes

Reaction equation

HRID 1968652 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([NH:20][C:29](=[O:30])[O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 59142793N4-(3-ethynylphenyl)-7-fluoroquinazoline-4,6-diamine

Product 1

HCID 59142774Phenyl 4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N4-(3-ethynylphenyl)-7-fluoroquinazoline-4,6-diamine (50 mg, 0.18 mmol) was dissolved into DMF (2 mL) containing pyridine (17.5 μL, 0.21 mmol). Phenyl chloroformate (23 μL, 0.18 mmol) was added to the mixture at room temperature and stirred at 70° C. for 1 h to give phenyl 4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-ylcarbamate. N1-(2,2-diethoxyethyl)-N2,N2-diethylethane-1,2-diamine (42 mg, 0.18 mmol) was added and stirred at 70° C. for 2.5 h. After cooled to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was concentrated and purified with a silica column to give 45 mg (70%) of 1-(2,2-diethoxyethyl)-1-(2-(diethylamino)ethyl)-3-(4-(3-ethynylphenylamino)-7-fluoroquinazolin-6-yl)urea.

Sources & evidence

ORD record
ord-170c6e50f17a4e048d5a9e5b32ca2e3f
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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