1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86706475, compound

HRID 919607Notes

Reaction equation

HRID 919607 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([NH:8][C:9]2[C:10]3[CH:17]=[CH:16][N:15]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:49][C:50]1[CH:51]=[C:52]([NH:57][CH2:58][C:59](O)=[O:60])[CH:53]=[C:54]([Cl:56])[CH:55]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:49][C:50]1[CH:51]=[C:52]([NH:57][CH2:58][C:59]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([NH:8][C:9]3[C:10]4[CH:17]=[CH:16][N:15]([S:18]([C:21]5[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=5)(=[O:19])=[O:20])[C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:2]2)=[O:60])[CH:53]=[C:54]([Cl:56])[CH:55]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 118906762HCID 118906762, compound

Product 1

HCID 86706475HCID 86706475, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(azepan-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.6 g, 1.6 mmol), in DMF (10 mL) was added EDCI (335 mg, 1.9 mmol), HOBt (250 mg, 1.9 mmol), 2-(3,5-dichlorophenylamino)acetic acid (342 mg, 1.6 mmol) and DIEA (301 mg, 2.3 mmol) at 0° C. The reaction mixture was stirred at rt overnight, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4 and evaporated in vacuo to give the crude compound that purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (800 mg, 87%). LC-MS: m/z [M+1]=587.

Workup

  1. washwashed with water (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated in vacuo
  4. customto give the crude compound
  5. customthat purified by column chromatography (silica gel, gradient MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-80a5cf3f10e94968af72a483feed1a6a
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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