O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67334241, compound

HRID 1804821Notes

Reaction equation

HRID 1804821 reaction equation
FC(F)(F)[C:3]([O-:5])=[O:4].FC(F)(F)C([O-])=O.[NH2+]1C2(CC[N:22]([C:25]([C:27]3[CH:28]=[C:29]([CH:42]=[CH:43][C:44]=3[F:45])[CH2:30][NH+:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34](=[O:41])[CH:33]=[CH:32]3)=[O:26])[CH2:21][CH2:20]2)CCC1.[Cl-].[C:47]([C:50]1[CH:51]=C(C=C[C:67]=1F)C[NH+]1C2C(=CC=CC=2)C(=O)C=C1)(O)=O.CN(C(O[N:77]1N=N[C:79]2C=CC=C[C:78]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1(C(OCCCC)=O)CCNCC1>CN(C=O)C.CCOC(C)=O>[F:45][C:44]1[CH:43]=[CH:42][C:29]([CH2:30][N:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34](=[O:41])[CH:33]=[CH:32]2)=[CH:28][C:27]=1[C:25]([N:22]1[CH2:79][CH2:78][N:77]([C:3]([O:5][C:50]([CH3:51])([CH3:67])[CH3:47])=[O:4])[CH2:20][CH2:21]1)=[O:26]

Participants

7

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21963126Butyl piperazine-1-carboxylateHCID 87360584HCID 87360584, compoundHCID 87361355HCID 87361355, compound

Product 1

HCID 67334241HCID 67334241, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Example 1, A2 in DMF (0.3 M) was added TEA (2.4 eq.) and TBTU (1.3 eq.). The mixture was stirred for 20 min and tent-butyl piperazine-1-carboxylate was added (1.5 eq.). After 1 h the mixture was diluted with EtOAc and washed with water, s.s. NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound as an orange foam.

Workup

  1. washwashed with water, s.s
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ebd543675def44b09b6c9bb620c602ff
Source dataset
uspto-grants-2013_01
Patent number
US08354413B2

Reaction notes

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