Triethylamine → (R)-2-[4-(4-fluoro-phenyl)-piperazin-1-yl]-1-(4-methyl-2-oxo-2,3-dihydro-b enzoxazol-6-ylmethyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 1864618Notes

Reaction equation

HRID 1864618 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:14]=[C:15]1[N:21]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C@@H:31]([C:44](O)=[O:45])[CH2:32][C:33]3[CH:42]=[C:41]([CH3:43])[C:36]4[NH:37][C:38](=[O:40])[O:39][C:35]=4[CH:34]=3)=[O:29])[CH2:24][CH2:23]2)[CH2:20][CH2:19][C:18]2[CH:47]=[CH:48][CH:49]=[CH:50][C:17]=2[NH:16]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[O:14]=[C:15]1[N:21]([CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C@H:31]([CH2:32][C:33]3[CH:42]=[C:41]([CH3:43])[C:36]4[NH:37][C:38](=[O:40])[O:39][C:35]=4[CH:34]=3)[C:44]([N:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)=[O:45])=[O:29])[CH2:26][CH2:27]2)[CH2:20][CH2:19][C:18]2[CH:47]=[CH:48][CH:49]=[CH:50][C:17]=2[NH:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68608307(R)-1-carboxy-2-(4-methyl-2-oxo-2,3-dihydrobenzoxazol-6-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 16734708(R)-2-[4-(4-fluoro-phenyl)-piperazin-1-yl]-1-(4-methyl-2-oxo-2,3-dihydro-b enzoxazol-6-ylmethyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

234 mg (1.30 mmol) 1-(4-fluoro-phenyl)-piperazine were added to a solution of 600 mg (1.18 mmol) (R)-1-carboxy-2-(4-methyl-2-oxo-2,3-dihydrobenz-oxazol-6-yl)-ethyl 4-(2-oxo-1,2,4,5,-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 417 mg (1.30 mmol) TBTU, 183 μL (1.30 mmol) triethylamine in 10 mL DMF and the reaction mixture was shaken at RT. The reaction solution was purified by HPLC without any further working up, the fractions containing the product were combined and lyophilised.

Workup

  1. customThe reaction solution was purified by HPLC without
  2. additionthe fractions containing the product

Sources & evidence

ORD record
ord-cee0bdd030a54af0aff2e3701691bcbc
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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