Methylamine → HCID 59186982, compound

HRID 889316Notes

Reaction equation

HRID 889316 reaction equation
[O:1]=[C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[C:11]([CH:15]=2)[C:12]([OH:14])=O)=[CH:5][NH:4][N:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[CH:22]([N:25](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.CN>CN(C=O)C.C1COCC1>[CH3:22][NH:25][C:12](=[O:14])[C:11]1[CH:15]=[C:7]([C:6]2[C:2](=[O:1])[N:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[NH:4][CH:5]=2)[CH:8]=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 6329Methylamine2×HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59186976HCID 59186976, compound

Product 1

HCID 59186982HCID 59186982, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

45.0 mg (159 μmol) of the compound from Example 44 are dissolved in 1 ml DMF, 1.9 mg (16 μmol) 4-N,N-dimethylaminopyridine, 24.7 mg (191 μmol) N,N-diisopropylethylamine and 100 mg (191 μmol) (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate are added and the mixture is stirred at RT for 15 min. 120 μl (239 μmol) of a 2 M solution of methylamine in THF are added and the mixture is stirred overnight at RT. To bring the conversion to completion, a further 120 μl (239 μmol) of the 2 M solution of methylamine in THF are added and the mixture is stirred again overnight at RT. The reaction mixture is purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient).

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. stirringthe mixture is stirred again overnight at RT
  3. customThe reaction mixture is purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-c858964d92f24984bbcaf4e22f224365
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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