Triethylamine → HCID 9849051, compound

HRID 411293Notes

Reaction equation

HRID 411293 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]([CH2:17][C:18]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:16])[N:7]=[C:6]2[NH2:30].[O:31]1[CH2:35][CH2:34][CH2:33][CH:32]1[C:36](O)=[O:37].C(N(CC)CC)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[NH2:30][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[C:8]([N:15]([CH2:17][C:18]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:20][N:21]([C:36]([CH:32]3[CH2:33][CH2:34][CH2:35][O:31]3)=[O:37])[CH2:22][CH2:23]2)[CH3:16])[N:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 86079(+-)-Tetrahydro-2-furoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11486612HCID 11486612, compound

Product 1

HCID 9849051HCID 9849051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-N2-methyl-quinazoline-2,4-diamine 11 (210 mg), tetrahydro-2-furoic acid (70 mg) and triethylamine (180 μL) in dichloromethane was added BOP reagent (benzotriazol -1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate) (250 mg). The mixture was stirred at room temperature for 20 hours, evaporated to dryness, and distributed between ethyl acetate and water. The organic phase was washed with sodium bicarbonate, brine, and dried over sodium sulfate. The crude product was purified by flash chromatography to provide 1-(4-{[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-methyl}-4-phenyl-piperidin-1-yl)-1-(tetrahydro-furan-2-yl)-methanone 14, MS: 506 ([M+H]+), which was converted into the HCl salt: 180 mg as white crystals.

Workup

  1. customevaporated to dryness
  2. washThe organic phase was washed with sodium bicarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7fbd6f6ebcd64ef4a358601d16d89aa1
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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