Diisopropylethylamine → HCID 58493972, compound

HRID 2360491Notes

Reaction equation

HRID 2360491 reaction equation
[C:1]([CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)([OH:3])=O.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F.C(N(CC)C(C)C)(C)C.Cl.Cl.[C:51]([C:55]1[CH:56]=[C:57]([NH:83][S:84]([CH3:87])(=[O:86])=[O:85])[C:58]([O:81][CH3:82])=[C:59]([NH:61][C:62]([C:64]2[N:65]([CH3:80])[C:66]3[C:71]([CH:72]=2)=[CH:70][CH:69]=[CH:68][C:67]=3[CH2:73][N:74]2[CH2:79][CH2:78][NH:77][CH2:76][CH2:75]2)=[O:63])[CH:60]=1)([CH3:54])([CH3:53])[CH3:52]>CN(C)C=O.C(OCC)(=O)C.O>[C:51]([C:55]1[CH:56]=[C:57]([NH:83][S:84]([CH3:87])(=[O:86])=[O:85])[C:58]([O:81][CH3:82])=[C:59]([NH:61][C:62]([C:64]2[N:65]([CH3:80])[C:66]3[C:71]([CH:72]=2)=[CH:70][CH:69]=[CH:68][C:67]=3[CH2:73][N:74]2[CH2:75][CH2:76][N:77]([C:1](=[O:3])[CH2:4][N:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[CH2:78][CH2:79]2)=[O:63])[CH:60]=1)([CH3:54])([CH3:52])[CH3:53]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27356422-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acidHCID 66986035HCID 66986035, compound

Product 1

HCID 58493972HCID 58493972, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

110 mg tert-butyl 4-carboxymethyl-piperazine-1-carboxylate are dissolved in 2 ml N,N-dimethylformamide, combined with 135 mg O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate (TBTU) as well as 270 μl N,N-diisopropyl-ethylamine (DIEA) and stirred for 20 minutes. Then 200 mg 1-methyl-7-piperazin-1-ylmethyl-1H-indole-2-carboxylic acid-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide dihydrochloride are added, the mixture is stirred for 12 hours at ambient temperature and then divided between water and ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (dichloromethane/(methanol/conc. ammonia 9:1) 99:1 to 90:10).

Workup

  1. stirringthe mixture is stirred for 12 hours at ambient temperature
  2. washThe organic phase is washed with saturated aqueous sodium chloride solution
  3. customdried on magnesium sulphate
  4. customthe residue is chromatographed on silica gel (dichloromethane/(methanol/conc. ammonia 9:1) 99:1 to 90:10)

Sources & evidence

ORD record
ord-171033dbfdef4acb9493fa8a5ddeb93a
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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