Benzylamine → HCID 59186974, compound

HRID 1526100Notes

Reaction equation

HRID 1526100 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=2)[C:10]([OH:12])=O)[NH:5][CH:4]=[C:3]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH2:64]([NH2:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C=O)C>[CH2:64]([NH:71][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][N:15]=[C:7]([N:6]2[C:2](=[O:1])[C:3]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:4][NH:5]2)[CH:8]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

6

Reactant 4

HCID 7504Benzylamine2×HCID 81531Diisopropylethylamine2×HCID 2724699PyBOP2×HCID 59186979HCID 59186979, compound

Product 1

HCID 59186974HCID 59186974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60.0 mg (213 μmol) of the compound from Example 41 are dissolved in 24 ml DMF, 2.6 mg (21 μmol) 4-N,N-dimethylaminopyridine, 65.9 mg (510 μmol) N,N-diisopropylethylamine and 265 mg (510 μmol) (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate are added and the mixture is stirred at RT for 45 min. 68.3 mg (638 μmol) benzylamine are added and the mixture is stirred overnight at RT. To bring the conversion to completion, a further 65.9 mg (510 μmol) N,N-diisopropylethylamine and 265 mg (510 μmol) (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate are added, the mixture is stirred at RT for 45 min, a further 68.3 mg (638 μmol) benzylamine are added and the mixture is then stirred overnight at RT. It is concentrated and the residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid).

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. stirringthe mixture is stirred at RT for 45 min
  3. stirringthe mixture is then stirred overnight at RT
  4. concentrationIt is concentrated
  5. customthe residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-9bfcad1fd85949c18b974e933c971784
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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