Water → 2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-4,5-difluorobenzyl acetate

HRID 1631167Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[N:15]=[C:14]([C:16]([N:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:27]3[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=3[CH2:35][OH:36])[CH:12]=2)[N:7]=1.C(OCC)(=O)C.O>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([O:36][CH2:35][C:28]1[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:27]=1[C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([NH2:5])[N:15]=[C:14]2[C:16]([N:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26]1)=[O:17])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

27 μl of acetyl chloride are added to a solution of 150 mg of [2-amino-6-(4,5-difluoro-2-hydroxymethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone and 2 mg of 4-(dimethylamino)pyridine (DMAP) in 5 ml of dimethylformamide, and the mixture is stirred at 80° C. for 16 h. 8 ml of ethyl acetate and 8 ml of water are added, the organic phase is separated off and evaporated to dryness in vacuo. The residue is dissolved in 1 ml of dimethyl sulfoxide and purified by chromatography (reversed phase HPLC).

Workup

customthe organic phase is separated off
customevaporated to dryness in vacuo
dissolutionThe residue is dissolved in 1 ml of dimethyl sulfoxide
custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record: ord-04463c57d3a84a08916b03cefa238ee3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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