Hydrochloric Acid → HCID 68227613, compound

HRID 1400139Notes

Reaction equation

HRID 1400139 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]2)=[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]([C:15]3([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]3)[CH:11]=2)[N:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 25953Cesium fluorideHCID 70473Bis(trimethylsilyl)carbodiimideHCID 68227402HCID 68227402, compound

Product 1

HCID 68227613HCID 68227613, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.2 g of ethyl 1-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]cyclobutanecarboxylate are dissolved in 50 ml of acetonitrile under argon. 370 mg of caesium fluoride and 679 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 3 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 g (99%) of ethyl 1-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]cyclobutanecarboxylate (oil);

Workup

  1. washThe aqueous phase is washed 3 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-f1ec916d1e134aedb0178c3d79c9caa6
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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