N,N-Dimethyl-1,3-propanediamine → HCID 67527701, compound

HRID 2388641Notes

Reaction equation

HRID 2388641 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:21][C:22]1[C:27]([NH2:28])=[CH:26][N:25]=[C:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[N:23]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1.CN(C)CCCN>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:21][C:22]1[C:27]([NH:28][S:42]([C:39]2[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=2)(=[O:44])=[O:43])=[CH:26][N:25]=[C:24]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[N:23]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:20])[N:17]([CH3:18])[CH3:19])=[CH:11][CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 67527329HCID 67527329, compound

Product 1

HCID 67527701HCID 67527701, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A pyridine (120 mL) solution of 2-(2-diethylamino-5-aminopyrimidin-4-ylamino)-3-(4-dimethylcarbamoyloxy-phenyl)propionic acid t-butyl ester (32.0 g, 0.067 mol) was cooled to −20° C. with a dry ice/CH3CN bath. The mixture stirred for 30 minutes, and then p-fluorobenzenesulfonyl chloride (13.18 g, 0.067 mol) was added slowly. The reaction was stirred at −20° C. for 4.5 hrs, and then 3-dimethylaminopropyl amine (8.52 mL, 0.067 mol) was added, and then the mixture was allowed to warm to room temperature overnight. The reaction was concentrated in vacuo. The residue was taken up in EtOAc (1 L), and the organic phase was washed with 0.5 M citric acid (3×900 mL), water (1×900 mL), sat. NaHCO3 (3×900 mL), brine (1×900 mL), dried (MgSO4), filtered, and concentrated in vacuo to yield a brown residue. The residue was purified by flash chromatography (50% EtOAc/hexanes on silica gel) to yield 33.04 g (77%) the title compound as a yellow foam. Rf=0.54 (3:2 EtOAc/hexanes on silica gel).

Workup

  1. stirringThe reaction was stirred at −20° C. for 4.5 hrs
  2. concentrationThe reaction was concentrated in vacuo
  3. washthe organic phase was washed with 0.5 M citric acid (3×900 mL), water (1×900 mL), sat. NaHCO3 (3×900 mL), brine (1×900 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown residue
  8. customThe residue was purified by flash chromatography (50% EtOAc/hexanes on silica gel)

Sources & evidence

ORD record
ord-3b25f717785f4b34b32cfd5695006534
Source dataset
uspto-grants-2012_09
Patent number
US08269009B2

Reaction notes

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