Cyclopentylamine → HCID 69084687, compound

HRID 1425676Notes

Reaction equation

HRID 1425676 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[O:21][C@H:20]3[C@H:16]([N:17]=[C:18]([N:22]4[CH2:25][CH2:24][CH2:23]4)[S:19]3)[C@@H:15]([OH:26])[C@@H:14]2[OH:27])(=O)=O)=CC=1.[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>>[N:22]1([C:18]2[S:19][C@H:20]3[O:21][C@H:13]([CH2:12][NH:33][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[C@@H:14]([OH:27])[C@H:15]([OH:26])[C@H:16]3[N:17]=2)[CH2:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 86707004HCID 86707004, compound

Product 1

HCID 69084687HCID 69084687, compoundYield 11%

Procedure

A solution of ((3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methyl 4-methylbenzenesulfonate (350 mg, 0.85 mmol) in cyclopentanamine (3 mL) was heated to 50° C. for overnight. The reaction mixture was condensed under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, x-Bridge 19*50 mm; mobile phase, Water with 0.05% NH4OH and CH3CN (15% CH3CN up to 28.6% in 5 min Flow rate 20 mL/min; Detector, UV 220 nm)] to give compound 5 as a light yellow solid (30 mg, 11%). (ES, m/z) [M+H]+ 328.0; 1H NMR (300 MHz, DMSO+D2O) 6.25-6.27 (d, J=6.3 Hz, 1H), 3.97 (m, 1H), 3.86 (m, 4H), 3.71 (m, 1H), 3.45 (m, 1H), 3.25 (m, 1H), 2.95 (m, 1H), 2.75 (m, 1H), 2.55 (m, 1H), 2.23 (m, 2H), 1.56-1.72 (m, 6H), 1.25 (m, 2H).

Workup

  1. customcondensed under vacuum
  2. customto give a residue, which
  3. customwas purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC)

Sources & evidence

ORD record
ord-8f393d084e5b4b508bc9696982236847
Source dataset
uspto-grants-2015_01
Patent number
US08933040B2

Reaction notes

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