Carbonic acid--N,N-diethylethanamine (1/2) → HCID 68817271, compound

HRID 656887Notes

Reaction equation

HRID 656887 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[N:36]=5)[CH:31]=[CH:30][C:29]4=[O:40])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O.C(O)(C(F)(F)F)=O.[Cl:66]CCl>>[ClH:66].[ClH:66].[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[N:36]=5)[CH:31]=[CH:30][C:29]4=[O:40])[CH2:24][CH2:25]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 21863450Trifluoroacetic acid methylene chlorideHCID 69185926HCID 69185926, compound

Product 1

HCID 68817271HCID 68817271, compound

Procedure

A solution of 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)(1-{2-[7-(methyloxy)-2-oxo-1,8-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)carbamate (160 mg, 0.3 mmol) in TFA/dichloromethane (2 ml/2 ml) was allowed to stand at room temperature for 1 hour then evaporated to dryness, azeotroping with chloroform. The residue was dissolved in dichloromethane/methanol (10 ml/10 ml) and treated with MP-carbonate resin (2.5 mmol of carbonate per gramme, 4 g, 10 mmol). After 15 minutes the mixture was filtered, washing with dichloromethane then methanol (twice) followed by evaporation affording the free base of the title compound.

Workup

  1. customthen evaporated to dryness
  2. customazeotroping with chloroform
  3. dissolutionThe residue was dissolved in dichloromethane/methanol (10 ml/10 ml)
  4. filtrationAfter 15 minutes the mixture was filtered
  5. washwashing with dichloromethane
  6. custommethanol (twice) followed by evaporation

Sources & evidence

ORD record
ord-09d49428494b457290e5cc7d9526f2c4
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…