1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178456039, compound

HRID 578964Notes

Reaction equation

[CH3:1][C@@H:2]([NH2:5])[CH2:3][CH3:4].[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][N:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][N:21]=3)[C:18]=2[OH:19])=[C:10]([CH3:29])[CH:9]=1)#[N:7].C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C@H:2]([NH:5][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([N:17]2[C:18]([OH:19])=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]#[N:7])=[CH:9][C:10]=3[CH3:29])[CH:15]=[N:16]2)=[N:21][CH:22]=1)([CH2:3][CH3:4])[CH3:1]

Participants

Conditions

Temperature: 50 °C

Procedure

Combined (R)-butan-2-amine (22.8 mg, 0.312 mmol) and a solution consisting of 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50 mg, 0.156 mmol), HOBT hydrate (35.9 mg, 0.234 mmol), EDCI (44.9 mg, 0.234 mmol), and Hunig's base (0.103 mL, 0.624 mmol) in DMA (1 mL) and stirred at 50° C. for 4 h. The reaction mixture was then purified via preparative HPLC to give the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90 (t, J=7.45 Hz, 3 H) 1.17 (d, J=6.57 Hz, 3 H) 1.44-1.63 (m, 2 H) 2.44 (s, 3 H) 3.95 (dt, J=14.02, 7.14 Hz, 1 H) 7.57-7.90 (m, 3 H) 7.92-8.73 (m, 4 H) 8.82-8.97 (m, 1 H) 13.20 (br. s., 1 H). MS m/z [M+H]+ 376.

Workup

customThe reaction mixture was then purified via preparative HPLC

Sources & evidence

ORD record: ord-a54107fffd9d4c388456d4212d9d5bbb
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040522B2

Reaction notes

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