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HCID 22466694, compound → HCID 10202344, compound

HRID 1935134
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Reaction equation

HRID 1935134 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:33]#[N:34])[CH:5]=[CH:6][CH:7]=1>C(O)(=O)C.O1CCCC1.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:33]#[N:34])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 22466694HCID 22466694, compound

Product 1

HCID 10202344HCID 10202344, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

N-[4-[(3-Bromophenyl)amino]-3-cyano-6-quinolinyl]-4-t-butyldimethylsiloxy-2-butynamide (60mg, 0.122 mmol) was dissolved in a solution of acetic acid, tetrahydrofuran and water (3:1:1) and stirred overnight at room temperature. The solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine. The ethyl acetate was concentrated to give 42.2 mg (90%) of yellow solid;: mass spectrum (electrospray, m/e,): 421.0311 (M+).

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. concentrationThe ethyl acetate was concentrated

Sources & evidence

ORD record
ord-3cc8b182471a460987cf904c9441742c
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06384051B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes