1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178510272, compound

HRID 872548Notes

Reaction equation

HRID 872548 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[C:15]([F:17])[C:12]([C:13]#[N:14])=[C:11]([F:18])[CH:10]=2)=[N:5]1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH2:26][C:27]([C:30](O)=[O:31])=[N:28][N:29]=2)[CH:20]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>>[C:13]([C:12]1[C:11]([F:18])=[CH:10][C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][CH2:2][NH:1][C:30]([C:27]3[CH:26]=[C:25]([C:21]4[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=4)[NH:29][N:28]=3)=[O:31])[N:5]=2)=[CH:16][C:15]=1[F:17])#[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 671716754-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile

Product 1

HCID 178510272HCID 178510272, compoundYield 18.5%

Procedure

The title compound was prepared from 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile (0.3 g, 0.773 mmol), 5-pyridin-3-yl-4H-pyrazole-3-carboxylic acid (0.161 g, 0.851 mmol), DIPEA (0.202 ml, 1.160 mmol), HOBt (0.157 g, 1.160 mmol) and EDCI (0.222 g, 1.160 mmol) using the method of Example 34(d) affording 0.06 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 3.70 (t, 2H), 4.39 (t, 2H), 7.01 (d, 1H), 7.79 (m, 2H), 7.88 (d, 1H).

Sources & evidence

ORD record
ord-b93f4cd100fd46caa656b255e598633a
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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