Triethylamine → (2R,4S)-N-[1-(3,5-Bis-trifluoromethyl-benzoyl)-2-benzyl-piperidin-4-yl]-quinazoline-4-carboxamide

HRID 1738913Notes

Reaction equation

HRID 1738913 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[N:53]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:56]([C:63](O)=[O:64])=[N:55][CH:54]=1>C(Cl)Cl>[F:28][C:26]([F:29])([F:27])[C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=1)[C:15]([N:9]1[CH2:10][CH2:11][C@H:12]([NH:14][C:63]([C:56]2[C:57]3[C:62](=[CH:61][CH:60]=[CH:59][CH:58]=3)[N:53]=[CH:54][N:55]=2)=[O:64])[CH2:13][C@H:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 22869971(2R,4S)-2-benzyl-1-(3,5-bis-(trifluoromethyl)benzoyl)-4-piperidinamineHCID 23008716Quinazoline-4-carboxylic acid

Product 1

HCID 18392943(2R,4S)-N-[1-(3,5-Bis-trifluoromethyl-benzoyl)-2-benzyl-piperidin-4-yl]-quinazoline-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 1, 252 mg (1.45 mmol) of (2R,4S)-2-benzyl-1-(3,5-bis-trifluoromethyl-benzoyl)-4-piperidineamine in 5 ml of methylene chloride are reacted with 368 mg (1.45 mmol) of bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride, 440 mg (4.35 mmol) of triethylamine and 566 mg (1.32 mmol) of quinazoline-4-carboxylic acid. The title compound is obtained in the form of white crystals. M.p.: 92-172° C.; TLC: hexane/ethyl acetate (1:1) Rf =0.37, FD-MS: M+ =586; [alpha]D=+1.3 (c=0.98, methylene chloride). ##STR16##

Sources & evidence

ORD record
ord-80a2adb8846940f9ae3bfcc6e0193f32
Source dataset
uspto-grants-1999_10
Patent number
US05965562

Reaction notes

Loading…