Diisopropylethylamine → HCID 57660946, compound

HRID 1424312Notes

Reaction equation

HRID 1424312 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:29][C:30]([NH:32][CH:33]([CH2:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)[C:34]([OH:36])=[O:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:47]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCCl.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Cu+2].CO.CCN(CC)CC>[CH3:47][O:36][C:34](=[O:35])[CH:33]([NH:32][C:30]([O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([N:18]2[CH2:19][CH2:20][CH:15]([CH2:14][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH2:16][CH2:17]2)=[CH:40][CH:39]=1

Participants

10

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 10088792HCID 10088792, compoundHCID 57660950HCID 57660950, compound

Product 1

HCID 57660946HCID 57660946, compound

Reagents, catalysts & solvents 5

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.7 g (9.3 mmol) Cu(OAc)2 and 26 ml NEt3 together with 900 mg (3.1 mmol) of (2) were suspended in 300 ml DCE. After adding 1.7 g (9.3 mmol) of (1) the mixture was stirred 18 h and the solvent was removed. The remaining oil was dissolved in ethyl acetate, washed with sodium acetate buffer (pH 4) and dried over Na2SO4. The solvent was removed under reduced pressure. The crude product was dissolved in 50 ml DMF and stirred with 4.7 g (12.4 mmol) HATU, 3.18 ml (18.6 mmol) DIPEA and 10 ml MeOH for 4 hours. Same amounts of HATU and DIPEA were added and the reaction mixture was stirred for 4 h at room temperature. After diluting with 300 ml ethyl acetate and washing four times with 2 N NaOH/brine (2:1) and with brine the solution was dried over Na2SO4 and concentrated in vacuo. Chromatography on silica gel with hexane/ethyl acetate was used to obtain pure (3).

Workup

  1. customthe solvent was removed
  2. dissolutionThe remaining oil was dissolved in ethyl acetate
  3. washwashed with sodium acetate buffer (pH 4)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. dissolutionThe crude product was dissolved in 50 ml DMF
  7. stirringthe reaction mixture was stirred for 4 h at room temperature
  8. washwashing four times with 2 N NaOH/brine (2:1)
  9. dry with materialwith brine the solution was dried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f14a4ba1f28244d8b2076a42e58f49b4
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

Loading…