1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[2-[3-(4-cyano-3-methylphenyl)pyrazol-1-yl]ethyl]-3-pyridin-3-yl-1H-pyrazole-5-carboxamide

HRID 872507Notes

Reaction equation

HRID 872507 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:8][C:9]([C:12]([OH:14])=O)=[N:10][N:11]=2)[CH:2]=1.[NH2:15][CH2:16][CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([CH3:31])[CH:24]=2)=[N:19]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][CH2:16][NH:15][C:12]([C:9]3[NH:10][N:11]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:8]=3)=[O:14])[N:19]=2)=[CH:24][C:25]=1[CH3:31])#[N:28]

Participants

6

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27716325-(pyridin-3-yl)-4H-pyrazole-3-carboxylic acidHCID 671717044-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile

Product 1

HCID 70657171N-[2-[3-(4-cyano-3-methylphenyl)pyrazol-1-yl]ethyl]-3-pyridin-3-yl-1H-pyrazole-5-carboxamideYield 64%

Procedure

The title compound was prepared using the method of Example 31 using 5-pyridin-3-yl-4H-pyrazole-3-carboxylic acid (0.46 g; 2.43 mmol), 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile (0.50 g; 2.21 mmol), HOBt (0.45 g; 3.31 mmol), EDCI (0.64 g; 3.31 mmol) and 0.58 ml (3.31 mmol) of DIPEA as starting materials. After workup the product was precipitated out from DCM to give 0.56 g (64%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 3.67-3.76 (m, 2H), 4.33-4.41 (m, 2H), 6.85 (d, 1H), 7.22 (s, 1H), 7.49 (dd, 1H), 7.74-7.82 (m, 2H), 7.83 (d, 1H), 7.88 (broad s, 1H), 8.10-8.18 (m, 1H), 8.44-8.58 (m, 2H), 9.00 (broad s, 1H), 13.82 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customwas precipitated out from DCM

Sources & evidence

ORD record
ord-1cf2d29f6c8840ba8085e3dbc40cbc1b
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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