Triethylamine → 3-(4-(4-(3-Fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)prop-2-ynyl methanesulfonate

HRID 877091Notes

Reaction equation

HRID 877091 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]#[C:25][CH2:26][OH:27])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[Cl:28].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:39][S:40]([O:27][CH2:26][C:25]#[C:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:29]=[CH:30][CH:31]=[C:2]([F:1])[CH:3]=2)=[C:8]([Cl:28])[CH:9]=1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 675042393-(4-(4-(3-Fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)prop-2-yn-1-ol2×

Product 1

HCID 866684763-(4-(4-(3-Fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)prop-2-ynyl methanesulfonateYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)prop-2-yn-1-ol (compound 10.1, 800 mg), triethyl amine (0.4 mL) in dichloromethane (20 mL) at 0° C. was added MsCl (0.16 mL) and the reaction mixture was warmed to room temperature. The reaction was washed with saturated NaHCO3 aqueous solution and extracted with dichloromethane. The combined organic layer and extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with EtOAc to give the desired product. LCMS ESI(+) m/z: 513 (M+1). Yield: 43%.

Workup

  1. washThe reaction was washed with saturated NaHCO3 aqueous solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer and extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-cfb1cfc6682a424ea180127d8816a739
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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