1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-ethyl 2-((1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-yl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)acetate

HRID 919571Notes

Reaction equation

HRID 919571 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]([C:14]2[C:15]3[CH:22]=[CH:21][N:20]([S:23]([C:26]4[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=4)(=[O:25])=[O:24])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:54][C:55]1[CH:56]=[C:57]([NH:62][CH2:63][C:64](O)=[O:65])[CH:58]=[C:59]([Cl:61])[CH:60]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:54][C:55]1[CH:56]=[C:57]([NH:62][CH2:63][C:64]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]([C:14]3[C:15]4[CH:22]=[CH:21][N:20]([S:23]([C:26]5[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=5)(=[O:25])=[O:24])[C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2]2)=[O:65])[CH:58]=[C:59]([Cl:61])[CH:60]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 86706452(R)-ethyl 2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)acetate

Product 1

HCID 68070434(R)-ethyl 2-((1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-yl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)acetateYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-ethyl 2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)acetate (0.2 g, 0.44 mmol) in DMF (2 mL) was added EDCI (0.13 g, 0.66 mmol), HOBt (89 mg, 0.7 mmol), 2-(3,5-dichlorophenylamino)acetic acid (0.1 g, 0.5 mmol) and DIEA (0.12 mL, 0.66 mmol) at 0° C. The solution was stirred at rt overnight, diluted with EtOAc and washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a residue which was purified by column chromatography (silica gel gradient methanol in chloroform) to afford (0.09 g, 31%) the titled compound. LCMS [M+1]: 659.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas purified by column chromatography (silica gel gradient methanol in chloroform)

Sources & evidence

ORD record
ord-4b389a571a524c72a6eb9e2dfe3e1a8d
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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