(R)-1-Cyclopropylethylamine → HCID 178426450, compound

HRID 579000Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2].[CH:25]1([C@H:28]([NH2:30])[CH3:29])[CH2:27][CH2:26]1>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:30][C@@H:28]([CH:25]4[CH2:27][CH2:26]4)[CH3:29])=[O:21])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 7016286(R)-1-Cyclopropylethylamine

HCID 178426451HCID 178426451, compound

Product 1

HCID 178426450HCID 178426450, compound

Procedure

The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and (R)-1-cyclopropylethanamine 1H NMR (400 MHz, DMSO-d6) δ ppm 0.17-0.27 (m, 1 H) 0.27-0.36 (m, 1 H) 0.36-0.44 (m, 1 H) 0.44-0.53 (m, 1 H) 0.94-1.07 (m, 1 H) 1.25 (d, J=6.82 Hz, 3 H) 2.43 (s, 3 H) 3.42-3.57 (m, 1 H) 7.66 (dd, J=8.08, 1.52 Hz, 1 H) 7.69-7.75 (m, 1H) 7.78 (d, J=7.58 Hz, 1 H) 8.17 (br. s., 1 H) 8.43 (d, J=6.32 Hz, 2 H) 8.59 (d, J=8.08 Hz, 1H) 8.85-8.95 (m, 1 H) 13.19 (br. s., 1 H). MS m/z [M+H]+ 388.2.

Sources & evidence

ORD record: ord-0f448d5b5218424984f3e2f11e1cbf24
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040522B2

Reaction notes

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