Hydrochloric Acid → HCID 67154017, compound

HRID 1400156Notes

Reaction equation

HRID 1400156 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][CH2:22][CH2:23][CH3:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]=1[C:25](=O)[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29]1)=[O:27])=O)(C)(C)C.[F-].[Cs+].C[Si]([N:44]=[C:45]=[N:46][Si](C)(C)C)(C)C.Cl.C(=O)(O)[O-]>C(#N)C>[NH2:44][C:45]1[N:46]=[C:25]([C:26]([N:28]2[CH2:29][C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:36]2)=[O:27])[C:10]2[C:9](=[CH:14][CH:13]=[C:12]([CH:15]([CH2:21][CH2:22][CH2:23][CH3:24])[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 67154051HCID 67154051, compound

Product 1

HCID 67154017HCID 67154017, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.8 g of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]hexanoate are dissolved in 100 ml of acetonitrile under argon. 1.12 g of caesium fluoride and 2.01 ml 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: 3.2 g (99%) of ethyl 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]hexanoate (oil);

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-bd0416f2bbea4595a829cc03ce1e1f3d
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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