(1R,2S)-2-(Methoxymethyl)cyclopentan-1-amine → HCID 178495617, compound

HRID 526475Notes

Reaction equation

HRID 526475 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](O)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2].[CH3:25][O:26][CH2:27][C@H:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[NH2:33]>>[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:33][C@@H:29]4[CH2:30][CH2:31][CH2:32][C@@H:28]4[CH2:27][O:26][CH3:25])=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 28064059(1R,2S)-2-(Methoxymethyl)cyclopentan-1-amineHCID 178426451HCID 178426451, compound

Product 1

HCID 178495617HCID 178495617, compound

Procedure

The title compound was prepared in a manner similar to Example 74 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and (1R,2S)-2-(methoxymethyl)cyclopentanamine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42-1.60 (m, 2H) 1.60-1.83 (m, 3H) 1.84-2.01 (m, 1H) 2.20-2.37 (m, 1H) 2.44 (s, 3H) 3.19 (s, 3H) 3.20-3.27 (m, 1H) 3.40 (dd, J=9.35, 6.06 Hz, 2H) 4.43 (t, J=7.45 Hz, 1H) 7.67 (d, J=7.58 Hz, 1H) 7.74 (br. s., 1H) 7.81 (d, J=18.69 Hz, 1H) 8.24-8.70 (m, 3H) 8.88 (d, J=1.77 Hz, 1H) 13.24 (br. s., 1H). MS m/z [M+H]+ 432.2.

Sources & evidence

ORD record
ord-2d910ca59d93438fae4e782cc0b8d47e
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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