2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 11575484, compound

HRID 1254880Notes

Reaction equation

HRID 1254880 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:14].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=1>CN(C=O)C>[CH3:45][S:42]([C:39]1[CH:40]=[CH:41][C:36]([CH2:35][N:7]2[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:13]3[C:5]([CH2:4][C:3]([OH:2])=[O:15])=[C:6]2[CH3:14])=[CH:37][C:38]=1[C:46]([F:47])([F:49])[F:48])(=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetateHCID 67219140HCID 67219140, compound

Product 1

HCID 11575484HCID 11575484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (12.8 g, 62.8 mmol) in dry DMF (200 ml) under an inert atmosphere of Argon is added dropwise, BEMP (19.9 ml, 69.1 mmol) over five minutes. After stirring at room temperature for 1 hour, the resulting solution is added dropwise to a stirred solution of 1-bromomethyl-4-methanesulfonyl-3-trifluoromethyl-benzene (23.9 g, 75.4 mmol) and stirred for 18 hours. The reaction is concentrated in vacuo with toluene and the resulting oil is purified by chromatography on silica eluting with iso-hexane/acetone (15:1). The crude is further purified by dissolving in hot ethyl acetate and refluxing in the presence of charcoal for 5 minutes. The solution is filtered and the solvent is removed in vacuo. The resulting solid is re-crystallized from ethyl acetate/iso-hexane to yield the titled product as a white solid. (MH+ 441)

Workup

  1. stirringstirred for 18 hours
  2. concentrationThe reaction is concentrated in vacuo with toluene
  3. customthe resulting oil is purified by chromatography on silica eluting with iso-hexane/acetone (15:1)
  4. customThe crude is further purified
  5. dissolutionby dissolving in hot ethyl acetate
  6. temperaturerefluxing in the presence of charcoal for 5 minutes
  7. filtrationThe solution is filtered
  8. customthe solvent is removed in vacuo
  9. customThe resulting solid is re-crystallized from ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-2c20e9039e904701828e4db619eeb7fa
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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