1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68070462, compound

HRID 919604Notes

Reaction equation

HRID 919604 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([N:8]([CH3:18])[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:40][C:41]1[CH:42]=[C:43]([NH:48][CH2:49][C:50](O)=[O:51])[CH:44]=[C:45]([Cl:47])[CH:46]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[NH:15]1[C:11]2=[N:12][CH:13]=[N:14][C:9]([N:8]([CH:3]3[CH2:4][CH2:5][CH2:6][CH2:7][N:1]([C:50](=[O:51])[CH2:49][NH:48][C:43]4[CH:42]=[C:41]([Cl:40])[CH:46]=[C:45]([Cl:47])[CH:44]=4)[CH2:2]3)[CH3:18])=[C:10]2[CH:17]=[N:16]1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 67518290HCID 67518290, compound

Product 1

HCID 68070462HCID 68070462, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(azepan-3-yl)-N-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (350 mg, 1.4 mmol) in DMF (7 mL) was added EDCI (409 mg, 2.1 mmol), HOBt (287 mg, 2.1 mmol), 2-(3,5-dichlorophenylamino)acetic acid (312 mg, 1.4 mmol) and DIEA (0.5 mL, 2.8 mmol) at 0° C. The reaction mixture was stirred at rt overnight and diluted with water and ethyl acetate (3:1, 400 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 (325 mg 51%) the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 13.50 and 13.44 (2s, 1H), 8.25-8.19 (m, 2H), 6.74 (s, 1H), 6.68 (s, 1H), 6.62 (s, 1H), 6.36 (bs, 1H), 4.21-3.71 (m, 5H), 3.42-3.01 (m, 2H), 3.31 (s, 3H), 1.93-1.65 (m, 6H). LC-MS: m/z [M+1]=448.

Workup

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

Sources & evidence

ORD record
ord-4ad105f15910463b8f03a560140c7890
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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