1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69676479, compound

HRID 919603Notes

Reaction equation

HRID 919603 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[CH:17][C:10]=23)[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:39][C:40]1[CH:41]=[C:42]([NH:47][CH2:48][C:49](O)=[O:50])[CH:43]=[C:44]([Cl:46])[CH:45]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH:15]1[C:11]2=[N:12][CH:13]=[N:14][C:9]([NH:8][CH:3]3[CH2:4][CH2:5][CH2:6][CH2:7][N:1]([C:49](=[O:50])[CH2:48][NH:47][C:42]4[CH:41]=[C:40]([Cl:39])[CH:45]=[C:44]([Cl:46])[CH:43]=4)[CH2:2]3)=[C:10]2[CH:17]=[N:16]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 86706470HCID 86706470, compound

Product 1

HCID 69676479HCID 69676479, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(azepan-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (200 mg, 0.862 mmol) in DMF (4 mL) was added EDCI (196 mg, 1.03 mmol), HOBt (139 mg, 1.03 mmol), 2-(3,5-dichlorophenylamino)acetic acid (189 mg, 0.862 mmol) and DIEA (0.22 mL, 1.29 mmol) at 0° C. The reaction mixture was stirred overnight at rt, 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 (150 mg, 40%). 1H NMR (DMSO-d6, 400 MHz): δ 13.49-13.36 (m, 1H), 8.27-7.96 (m, 2H), 6.74 (s, 1H), 6.67 (s, 1H), 6.62 (s, 1H), 6.34 (s, 1H), 4.50-4.30 (m, 1H), 4.08-3.8 (m, 5H), 3.36 (m, 2H), 1.8-2.2 (m, 2H), 1.8-1.35 (m, 2H), 1.3-1.1 (m, 2H), LCMS: m/z [M+1]=434 & [M+23]=456.

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-7f20e591d04c417997c099ae8152c3a9
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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