2-(2-Bromoethoxy)tetrahydro-2H-pyran → HCID 58204352, compound

HRID 1498228Notes

Reaction equation

HRID 1498228 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:26]=[CH:25][C:8]3[O:9][CH2:10][CH2:11][C:12]4[N:13]([N:14]=[C:15]([C:17]5[N:21]([CH:22]([CH3:24])[CH3:23])[N:20]=[CH:19][N:18]=5)[CH:16]=4)[C:7]=3[CH:6]=2)[CH2:2]1.Br[CH2:28][CH2:29][O:30]C1CCCCO1>>[CH:22]([N:21]1[C:17]([C:15]2[CH:16]=[C:12]3[N:13]([C:7]4[CH:6]=[C:5]([CH:3]5[CH2:2][N:1]([CH2:28][CH2:29][OH:30])[CH2:4]5)[CH:26]=[CH:25][C:8]=4[O:9][CH2:10][CH2:11]3)[N:14]=2)=[N:18][CH:19]=[N:20]1)([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 58204723HCID 58204723, compound

Product 1

HCID 58204352HCID 58204352, compound

Procedure

Following the procedures of Example 142, 9-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene 144 was reacted with 2-(2-bromoethoxy)-tetrahydropyran followed by acidic hydrolysis of the THP group to give 169 as a white solid, as illustrated in FIG. 13. 1H NMR (400 MHz, DMSO-d6): δ 8.03 (s, 1 H); 7.88 (d, J=2.22 Hz, 1 H); 7.42 (dd, J=8.35, 2.22 Hz, 1 H); 7.26 (d, J=8.32 Hz, 1H); 6.89 (s, 1 H); 5.62-5.54 (m, 1 H); 4.83 (s, 1 H); 4.50 (t, J=6.03 Hz, 2 H); 4.06 (s, 2H); 3.94 (t, J=8.52 Hz, 1 H); 3.70 (s, 2 H); 3.51 (s, 3 H); 3.18 (t, J=6.05 Hz, 2 H); 2.94 (s, 2 H); 1.49 (d, J=6.58 Hz, 6 H). LCMS: RT=6.01 min, M+H+=395

Workup

  1. customfollowed by acidic hydrolysis of the THP group

Sources & evidence

ORD record
ord-acf83d758cfa4182b0a378cd82200252
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

Loading…