Hydrochloric Acid → HCID 67154052, compound

HRID 1400151Notes

Reaction equation

HRID 1400151 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][CH2:22][CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]=1[C:24](=O)[C:25]([N:27]1[CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28]1)=[O:26])=O)(C)(C)C.[F-].[Cs+].C[Si]([N:43]=[C:44]=[N:45][Si](C)(C)C)(C)C.Cl.C(=O)(O)[O-]>C(#N)C>[NH2:43][C:44]1[N:45]=[C:24]([C:25]([N:27]2[CH2:28][C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:35]2)=[O:26])[C:10]2[C:9](=[CH:14][CH:13]=[C:12]([CH:15]([CH2:21][CH2:22][CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]=2)[N:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 25953Cesium fluorideHCID 70473Bis(trimethylsilyl)carbodiimideHCID 67154074HCID 67154074, compound

Product 1

HCID 67154052HCID 67154052, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.4 g of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]pentanoate are dissolved in 50 ml of acetonitrile under argon. 431 mg of caesium fluoride and 769 μl of bis(trimethylsilyl)carbodiimide are added to the solution. The mixture is stirred at room temperature for 15 min, and 6 ml of hydrochloric acid (1N) are then added, and the mixture is neutralised using bicarbonate. The aqueous phase is washed three times with 100 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated to dryness in vacuo. Yield: 1.1 g (92%) of ethyl 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]pentanoate (oil); LC-MS retention time: 1.84 min (“nonpolar” gradient).

Workup

  1. washThe aqueous phase is washed three times with 100 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-c714b8a9b4f54a5bacad2f963b2db016
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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