1-Hydroxybenzotriazole → HCID 59814462, compound

HRID 2116690Notes

Reaction equation

HRID 2116690 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])([CH3:3])C.C[N:11](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH2:42][C:43]1[C:48]([CH3:49])=[CH:47][C:46]([CH2:50][C@@H:51]([NH:55][C:56]([N:58]2[CH2:63][CH2:62][CH:61]([N:64]3[CH2:70][CH2:69][C:68]4[CH:71]=[CH:72][CH:73]=[CH:74][C:67]=4[NH:66][C:65]3=[O:75])[CH2:60][CH2:59]2)=[O:57])[C:52](O)=[O:53])=[CH:45][C:44]=1[Cl:76].C1(N2CCNCC2)CC1.C(=O)([O-])O.[Na+]>CN(C=O)C.C1COCC1>[NH2:42][C:43]1[C:48]([CH3:49])=[CH:47][C:46]([CH2:50][C@@H:51]([NH:55][C:56]([N:58]2[CH2:63][CH2:62][CH:61]([N:64]3[CH2:70][CH2:69][C:74]4[CH:73]=[CH:72][CH:71]=[CH:68][C:67]=4[NH:66][C:65]3=[O:75])[CH2:60][CH2:59]2)=[O:57])[C:52]([N:11]2[CH2:6][CH2:5][N:4]([CH:7]3[CH2:9][CH2:8]3)[CH2:1][CH2:3]2)=[O:53])=[CH:45][C:44]=1[Cl:76]

Participants

9

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 47420041-CyclopropylpiperazineHCID 69193918HCID 69193918, compound

Product 1

HCID 59814462HCID 59814462, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.1 ml diisopropylethylamine, 64.2 mg (0.20 mmol) TBTU and 27.0 mg (0.20 mmol) HOBt was added to a mixture of 100 mg (0.20 mmol) (R)-3-(4-amino-3-chloro-5-methyl-phenyl)-2-([4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carbonyl]-amino)-propionic acid, 10 ml THF and 1 ml DMF, the mixture was stirred for 15 hours at ambient temperature and then combined with 80 mg (0.60 mmol) 1-cyclopropyl-piperazine. The reaction mixture was stirred for 3 hours at ambient temperature, combined with 20 ml semisaturated sodium hydrogen carbonate solution and extracted twice with 20 ml of ethyl acetate. The combined organic phases were washed once with 20 ml saturated saline solution, dried over sodium sulphate and evaporated down under reduced pressure. The residue was purified by column chromatography through silica gel.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at ambient temperature
  2. extractionextracted twice with 20 ml of ethyl acetate
  3. washThe combined organic phases were washed once with 20 ml saturated saline solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated down under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-352802bfbe5b499487f1967a15de779a
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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