Hydrochloric Acid → (2-Amino-6-iodoquinazolin-4-yl)isoindolin-2-ylmethanone

HRID 1631101Notes

Reaction equation

HRID 1631101 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10](=[O:28])[C:11]([C:13]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:14]=1[NH:20]C(=O)OC(C)(C)C)=O.[F-].[Cs+].C[Si]([N:35]=[C:36]=[N:37][Si](C)(C)C)(C)C.Cl>C(#N)C.ClCCl>[NH2:35][C:36]1[N:37]=[C:11]([C:10]([N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1]2)=[O:28])[C:13]2[C:14](=[CH:15][CH:16]=[C:17]([I:19])[CH:18]=2)[N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 70473Bis(trimethylsilyl)carbodiimideHCID 59483457Tert-butyl {2-[2-(1,3-dihydroisoindol-2-yl)-2-oxoacetyl]-4-iodophenyl}carbamate

Product 1

HCID 58457195(2-Amino-6-iodoquinazolin-4-yl)isoindolin-2-ylmethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

24.50 g of tert-butyl {2-[2-(1,3-dihydroisoindol-2-yl)-2-oxoacetyl]-4-iodophenyl}carbamate are dissolved in 500 ml of acetonitrile under argon. 0.756 g of caesium fluoride is added, and 16.887 ml of bis(trimethylsilyl)carbodiimide are added dropwise to the solution over the course of 5 min. The mixture is stirred at room temperature for 15 min, and 400 ml of dichloromethane are added. After addition of 400 ml of hydrochloric acid (1N), the product precipitates out as white solid; yield: 14 g of (2-amino-6-iodoquinazolin-4-yl)-(1,3-dihydroisoindol-2-yl)methanone; LC-MS retention time: 1.66 min;

Workup

  1. customthe product precipitates out as white solid

Sources & evidence

ORD record
ord-4fff02e4bc614ef6b5e63ada9fa71a78
Source dataset
uspto-grants-2014_07
Patent number
US08791129B2

Reaction notes

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