Triphenylphosphine → HCID 59199319, compound

HRID 2079666Notes

Reaction equation

HRID 2079666 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].[F:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]2[N:47]=[CH:46][C:45]3[C:40](=[CH:41][C:42](O)=[CH:43][CH:44]=3)[N:39]=2)=[CH:33][C:32]=1[CH3:49]>C1COCC1>[F:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]2[N:47]=[CH:46][C:45]3[C:40](=[CH:41][C:42]([O:29][CH:26]4[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]4)=[CH:43][CH:44]=3)[N:39]=2)=[CH:33][C:32]=1[CH3:49]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 136029924HCID 136029924, compound

Product 1

HCID 59199319HCID 59199319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (2 eq) in THF was added di-terbutylazodicarboxylate (2 eq). The mixture was stirred 15 minutes at ambient temperature under nitrogen atmosphere. To that was added 1-isopropylpiperidine-4-ol (5 eq). The mixture was stirred 15 minutes at ambient temperature followed by addition of 2-(4-fluoro-3-methylphenylamino) quinazolin-7-ol (1 eq). The mixture was stirred overnight at ambient temperature. The LC-MS of reaction mixture shows the presence of two product (2:1) with identical mass. The reaction mixture was concentrated and purified by semi-preparative HPLC to provide (N-(4-fluoro-3-methylphenyl)-7-(1-isopropyl-piperidin-4-yloxy)-quinazolin-2-amine as a major product ES/MS m/z 395.2 (MH+).

Workup

  1. stirringThe mixture was stirred 15 minutes at ambient temperature
  2. stirringThe mixture was stirred overnight at ambient temperature
  3. customThe LC-MS of reaction mixture
  4. concentrationThe reaction mixture was concentrated
  5. custompurified by semi-preparative HPLC

Sources & evidence

ORD record
ord-261ca0f177564a97bd50ada26d860329
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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