1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178509581, compound

HRID 872541Notes

Reaction equation

HRID 872541 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=2)=[N:5]1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH2:25][C:26]([C:29](O)=[O:30])=[N:27][N:28]=2)[CH:19]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>>[Cl:17][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][CH2:2][NH:1][C:29]([C:26]3[CH:25]=[C:24]([C:20]4[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=4)[NH:28][N:27]=3)=[O:30])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

6

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27716325-(pyridin-3-yl)-4H-pyrazole-3-carboxylic acidHCID 671701664-(1-(2-Aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 178509581HCID 178509581, compoundYield 3.6%

Procedure

The title compound was prepared from 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.361 g, 1.463 mmol), 5-Pyridin-3-yl-4H-pyrazole-3-carboxylic acid (0.305 g, 1.610 mmol), DIPEA (0.382 ml, 2.195 mmol), HOBt (0.297 g, 2.195 mmol) and EDCI (0.421 g, 2.195 mmol) using the method of Example 75(b) affording 0.022 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 3.71 (m, 2H), 4.38 (t, 2H), 6.97 (m, 1H), 7.23 (m, 1H), 7.48 (m, 1H), 7.86 (m, 2H), 7.97 (m, 1H), 8.09 (m, 1H), 8.17 (m, 1H), 8.40-8.71 (m, 2H), 8.98 (m, 1H), 13.82 (m, 1H).

Sources & evidence

ORD record
ord-18ffd957c03f429d914258dab09fcd0a
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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