1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178432537, compound

HRID 872822Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[NH:5][C:6]=1[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.[NH2:47][C@@H:48]([CH3:64])[CH2:49][N:50]1[CH:54]=[CH:53][C:52]([C:55]2[CH:62]=[CH:61][C:58]([C:59]#[N:60])=[C:57]([Cl:63])[CH:56]=2)=[N:51]1>CN(C=O)C.O>[Cl:63][C:57]1[CH:56]=[C:55]([C:52]2[CH:53]=[CH:54][N:50]([CH2:49][C@@H:48]([NH:47][C:7]([C:6]3[NH:5][C:4]([C:10]4[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=4)=[N:3][C:2]=3[CH3:1])=[O:9])[CH3:64])[N:51]=2)[CH:62]=[CH:61][C:58]=1[C:59]#[N:60]

Participants

Conditions

Temperature: 60 °C

Procedure

4-methyl-2-(pyridin-3-yl)-1H-imidazole-5-carboxylic acid (78 mg; 0.384 mmol) and DIPEA (0.20 ml, 1.151 mmol) were dissolved in 5 ml of dry DMF. HOBt hydrate (88 mg; 0.575 mmol) and EDCI (110 mg; 0.575 mmol) were added at RT. Solid (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (100 mg; 0.384 mmol) was added in one portion and the reaction was stirred for 2 h at 60° C. temperature and stirred at RT overnight. Water (40 ml) was added and the mixture was allowed to stir 1 h at RT. The precipitated product was filtered, dried in vacuum at 40° C. for 12 h, to give the title compound 136 mg. 1H-NMR (400 MHz; d6-DMSO): δ 1.12 (d, 3H), 2.49 (s, 3H), 4.40 (m, 3H), 6.97 (d, 1H), 7.48 (m, 1H), 7.88 (m, 2H), 8.02 (m, 2H), 8.07 (d, 1H), 8.21 (m, 1H), 8.58 (m, 1H), 9.13 (d, 1H), 12.85 (s, 1H).

Workup

stirringstirred at RT overnight
stirringto stir 1 h at RT
filtrationThe precipitated product was filtered
customdried in vacuum at 40° C. for 12 h

Sources & evidence

ORD record: ord-8df50f3bb98244e7a0254fdda29a04f1
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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