Azide → {7-[5-(1-Phenyl-cyclopentyl)-[1,2,3]triazol-1-yl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}-acetic acid

HRID 570642Notes

Reaction equation

HRID 570642 reaction equation
[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[N:14]([CH:17]1[CH2:36][N:21]2[C:22]3[C:27]([C:28]([CH2:29][C:30]([O:32]CCC)=[O:31])=[C:20]2[CH2:19][CH2:18]1)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N+:15]=[N-:16].[N-]=[N+]=[N-]>>[C:8]1([C:3]2([C:1]3[N:14]([CH:17]4[CH2:36][N:21]5[C:22]6[C:27]([C:28]([CH2:29][C:30]([OH:32])=[O:31])=[C:20]5[CH2:19][CH2:18]4)=[CH:26][CH:25]=[CH:24][CH:23]=6)[N:15]=[N:16][CH:2]=3)[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 33558AzideHCID 44118248(1-Ethynylcyclopentyl)benzeneHCID 59487226Propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

Product 1

HCID 46893926{7-[5-(1-Phenyl-cyclopentyl)-[1,2,3]triazol-1-yl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}-acetic acid

Procedure

The title compound was prepared using analogous procedures described in EXAMPLE 3 from (1-ethynylcyclopentyl)benzene and enantiomerically pure propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate, prepared by resolution of the racemic azide on a 4.6×250 mm ChiralCel OD column eluting with 15% MeOH, 15% iPrOH, 69.75% Hexanes and 0.25% Et3N at 1 mL/min and 254 nm. Retention times=10.3 and 11.5 min. EXAMPLE 6.1 and 6.2 were prepared from the chiral azide with the retention time of 10.3 and 11.5 min respectively. 1H NMR data of EXAMPLE 6.1: 1H NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1 H), 7.93 (s, 1 H), 7.42 (d, 1 H), 7.36 (dd, 2 H), 7.31-7.23 (m, 3 H), 7.13 (d, 1 H), 7.07-6.97 (m, 2 H), 4.59 (s, 1 H), 3.98-3.89 (m, 1 H), 3.58-3.46 (m, 2 H), 3.03-2.92 (m, 1 H), 2.29-2.20 (m, 1 H), 2.10-2.01 (m, 1 H), 1.54-1.43 (m, 1 H). MS (+ESI) m/z: 441.2.

Workup

  1. washeluting with 15% MeOH, 15% iPrOH, 69.75% Hexanes and 0.25% Et3N at 1 mL/min and 254 nm
  2. customRetention times=10.3 and 11.5 min
  3. customEXAMPLE 6.1 and 6.2 were prepared from the chiral azide with the retention time of 10.3 and 11.5 min respectively

Sources & evidence

ORD record
ord-16730301686445c896650d694aa8fdd2
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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