HCID 71735429, compound → HCID 71736408, compound

HRID 1615933Notes

Reaction equation

HRID 1615933 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:21]([CH2:24][CH:25]3[CH2:27][CH2:26]3)=[N:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[Cl:1][C:2]1[C:3]2[N:4]([C:21]([CH2:24][CH:25]3[CH2:26][CH2:27]3)=[N:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][C@H:10]1[CH2:14][CH2:13][CH2:12][C@@H:11]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 71735429HCID 71735429, compound

Product 1

HCID 71736408HCID 71736408, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic trans 8-chloro-3-(cyclopropylmethyl)-N-((2-phenylcyclopentyl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-7-amine was resolved by chiral preparative HPLC using a Chiralcel OJ 21×250 mm, 10 micron column with a 30% ethanol/0.1% diethylamine/heptane as the mobile phase to give 8-chloro-3-(cyclopropylmethyl)-N-(((1S,2S)-2-phenylcyclopentyl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-7-amine, peak 1, eluting at 6.8 min. 1H NMR (400 MHz, METHANOL-d4) δ 8.05 (d, J=7.5 Hz, 1H), 7.33-7.20 (m, 5H), 7.20-7.08 (m, 1H), 6.60 (d, J=7.8 Hz, 1H), 3.48-3.36 (m, 1H), 2.97 (d, J=7.0 Hz, 2H), 2.83-2.66 (m, 1H), 2.40 (d, J=8.0 Hz, 1H), 2.23-2.05 (m, 2H), 1.93-1.76 (m, 3H), 1.57 (dd, J=12.7, 7.2 Hz, 1H), 1.26-1.13 (m, 1H), 0.70-0.56 (m, 2H), 0.39-0.25 (m, 2H). LCMS: M+1=381.16.

Sources & evidence

ORD record
ord-4e3ce09e266f4b8eb99b6e5218ed0caa
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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