Hydrochloric Acid → HCID 52939424, compound

HRID 1400133Notes

Reaction equation

HRID 1400133 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16]2)=[CH:11][C:10]=1[C:23](=O)[C:24]([N:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27]1)=[O:25])=O)(C)(C)C.[F-].[Cs+].C[Si]([N:42]=[C:43]=[N:44][Si](C)(C)C)(C)C.Cl>C(#N)C>[NH2:42][C:43]1[N:44]=[C:23]([C:24]([N:26]2[CH2:27][C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:34]2)=[O:25])[C:10]2[C:9](=[CH:14][CH:13]=[C:12]([C:15]3([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16]3)[CH:11]=2)[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 70473Bis(trimethylsilyl)carbodiimideHCID 68227310HCID 68227310, compound

Product 1

HCID 52939424HCID 52939424, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

670 mg of ethyl 1-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]cyclopropanecarboxylate are dissolved in 15 ml of acetonitrile under argon. 213 mg of caesium fluoride and 380 μl of bis(trimethylsilyl)carbodiimide are added to the solution. The mixture is stirred at room temperature for 15 min, and 2.7 ml of hydrochloric acid (1N) are then added, with the product precipitating as white solid. Yield: 510 mg (91%) of ethyl 1-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]cyclopropanecarboxylate; LC-MS retention time: 1.65 min (“nonpolar” gradient);

Workup

  1. customprecipitating as white solid

Sources & evidence

ORD record
ord-86659e27daa74e79ab40bfa0b8c22e54
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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