Triethylamine → (S)-3-Hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid tetrahydro-furan-3-yl ester

HRID 2079268Notes

Reaction equation

HRID 2079268 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=2)[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[N:10]=1.[O:27]1[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28]1.Cl[C:34]([O-])=[O:35].C(N(CC)CC)C>C(Cl)Cl.O>[O:27]1[CH2:31][CH2:30][CH:29]([O:32][C:34]([N:7]2[CH2:6][CH2:5][N:4]([C:9]3[C:18]4[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=4)[N:12]=[C:11]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])[N:10]=3)[C@H:3]([CH2:2][OH:1])[CH2:8]2)=[O:35])[CH2:28]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86606942(S)-tetrahydro-furan-3-ol chloroformateHCID 1361213512-[4-(2-Hydroxymethyl-piperazin-1-yl)-7-methyl-quinazolin-2-yl]-phenol

Product 1

HCID 136366916(S)-3-Hydroxymethyl-4-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperazine-1-carboxylic acid tetrahydro-furan-3-yl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 2-[4-(2-hydroxymethyl-piperazin-1-yl)-7-methyl-quinazolin-2-yl]-phenol (69.2 mg, 0.19 mmol) in 650 μL of CH2Cl2 at 0° C. was added (S)-tetrahydro-furan-3-ol-chloroformate (26.8 mg, 0.17 mmol), followed by triethylamine (30 μL, 0.22 mmol). The reaction mixture was stirred for an hour and then diluted with 5 mL of CH2Cl2 and 5 mL of water, and the organic layer was separated and dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was subjected to purification using 30-100% EtOAc-hexanes to give the desired product. LC/MS: m/z 465.2 (M+H)+ at 2.5 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was subjected to purification

Sources & evidence

ORD record
ord-ec7f1afeb2ec462e89e80defb2775d0e
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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