1-Hydroxybenzotriazole → HCID 57529761, compound

HRID 643605Notes

Reaction equation

HRID 643605 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:28](O)=[O:29])[CH2:19][C:20]3[CH:25]=[C:24]([Br:26])[CH:23]=[C:22]([Br:27])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:31]=[CH:32][CH:33]=[CH:34][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:76][N:77]([CH3:84])[CH:78]1[CH2:83][CH2:82][NH:81][CH2:80][CH2:79]1>CN(C=O)C.O>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:25]=[C:24]([Br:26])[CH:23]=[C:22]([Br:27])[CH:21]=3)[C:28]([N:81]3[CH2:82][CH2:83][CH:78]([N:77]([CH3:84])[CH3:76])[CH2:79][CH2:80]3)=[O:29])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:31]=[CH:32][CH:33]=[CH:34][C:4]=2[NH:3]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67301185HCID 67301185, compound

Product 1

HCID 57529761HCID 57529761, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 150 mg (0.25 mmol) of (R)-1-carboxy-2-(3,5-dibromo-phenyl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 90 mg (0.28 mmol) TBTU, 95 μL (0.55 mmol) ethyldiisopropylamine and 38 mg (0.28 mmol) HOBt in 6 mL DMF was stirred for 90 min at RT. Then 42 mg (0.33 mmol) 4-dimethylamino-piperidine were added and the reaction mixture was stirred for 16 h at RT. The reaction solution was combined with water, the organic phase was evaporated down and the residue was purified by chromatography (silica gel, DCM/MeOH/NH3 95:5:0.5).

Workup

  1. customthe organic phase was evaporated down
  2. customthe residue was purified by chromatography (silica gel, DCM/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-581acb5023b04f1da9a655d0fe0a8092
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

Loading…