N-BOC-ethylenediamine → HCID 57602418, compound

HRID 1788335Notes

Reaction equation

HRID 1788335 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[C:34]([O:38][C:39](=[O:44])[NH:40][CH2:41][CH2:42][NH2:43])([CH3:37])([CH3:36])[CH3:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:34]([O:38][C:39](=[O:44])[NH:40][CH2:41][CH2:42][NH:43][C:29](=[O:30])[C:28]1[CH:27]=[CH:26][C:25]([C:21]2[CH:20]=[C:19]3[C:24]([C:15]([C:8]4[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)=[N:11][N:10]5[CH2:12][CH2:13][CH2:14][C:9]=45)=[CH:16][CH:17]=[N:18]3)=[CH:23][CH:22]=2)=[CH:33][CH:32]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69056216HCID 69056216, compound

Product 1

HCID 57602418HCID 57602418, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yl]-benzoic acid (Example 41 before reverse phase chromatography, 0.08 g, 0.185 mmol), (2-aminoethyl)-carbamic acid tert-butyl ester (0.036 g, 0.2 mmol), N—N-Diisopropylethylamine (0.08 mL, 0.46 mmol) and HBTU (0.076 g, 0.2 mmol) are mixed in 10 mL of DMF and stirred at RT for 8 h under nitrogen. The crude mixture is diluted with EtOAc (30 mL) and extracted with saturated NaHCO3. The organic phase is separated and washed with saturated brine, dried (Na2SO4), filtered, evaporated to a solid mass. The crude product is purified by MPLC on silica gel (80% EtOAc/Hexanes, 1% MeOH) to yield the title compound, 0.059 g (56%), as white solid.

Workup

  1. extractionextracted with saturated NaHCO3
  2. customThe organic phase is separated
  3. washwashed with saturated brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to a solid mass
  7. customThe crude product is purified by MPLC on silica gel (80% EtOAc/Hexanes, 1% MeOH)

Sources & evidence

ORD record
ord-f998128849b945c88d02b7863ec5f63c
Source dataset
uspto-grants-2009_03
Patent number
US07511065B2

Reaction notes

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