Triethylamine → diethyl 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonate

HRID 736927Notes

Reaction equation

HRID 736927 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12]([CH2:19][C:20]([C:30]([O:32][CH2:33][CH3:34])=[O:31])([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][C:22]([OH:24])=O)=[CH:11][C:10]=1[Cl:35].[NH:36]1[CH2:41][CH2:40][CH:39]([N:42]2[CH2:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[NH:44][C:43]2=[O:52])[CH2:38][CH2:37]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[NH2:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12]([CH2:19][C:20]([CH2:21][C:22](=[O:24])[N:36]2[CH2:37][CH2:38][CH:39]([N:42]3[CH2:51][C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[NH:44][C:43]3=[O:52])[CH2:40][CH2:41]2)([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:11][C:10]=1[Cl:35]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 221846134-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butanoic acid

Product 1

HCID 68592549diethyl 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.2 mL (23.0 mmol) of triethylamine were added dropwise to a solution of 8.00 g (19.0 mmol) of 4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butanoic acid, 4.39 g (19.0 mmol) of 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one, 6.00 g (18.0 mmol) of TBTU and 2.75 g (18.0 mmol) of HOBT in 100 mL of THF and the mixture was stirred for 16 h at RT. The solid formed was filtered off, washed with diethyl ether and dried i. vac.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with diethyl ether
  4. customdried i

Sources & evidence

ORD record
ord-94ae479aaf504f52b844887f07e28b27
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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