3-Oxa-8-azabicyclo(3.2.1)octane hydrochloride → 8-(4-(4-(Tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4,3-c]pyridin-3-yl)pyridin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane

HRID 1046500Notes

Reaction equation

HRID 1046500 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:12]3[C:13]([O:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:14][CH:15]=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.Cl.[CH:44]12[NH:51][CH:48]([CH2:49][CH2:50]1)[CH2:47][O:46][CH2:45]2>>[O:21]1[CH2:20][CH2:19][CH:18]([O:17][C:13]2[C:12]3[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([N:51]5[CH:44]6[CH2:50][CH2:49][CH:48]5[CH2:47][O:46][CH2:45]6)[CH:7]=4)=[N:9][NH:10][C:11]=3[CH:16]=[CH:15][N:14]=2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 534011293-Oxa-8-azabicyclo(3.2.1)octane hydrochlorideHCID 866736963-(2-Chloropyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 668291728-(4-(4-(Tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4,3-c]pyridin-3-yl)pyridin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octaneYield 24%

Procedure

Prepared according to the procedure described in Example 111, by reacting 3-(2-chloropyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine with 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride for 100 minutes in Step 1 to give the title compound (14.2 mg, 24% over two steps). LC-MS (Method G): m/z=408.1 [M+H]+; 3.32 min. 1H-NMR (400 MHz, DMSO): δ 13.40 (s, 1H), 8.19 (d, J=4.3, 1H), 7.90 (d, J=5.7, 1H), 7.28 (s, 1H), 7.24-7.13 (m, 2H), 5.54-5.45 (m, 1H), 4.51 (s, 2H), 3.86-3.73 (m, 2H), 3.70 (d, J=10.6, 2H), 3.59-3.46 (m, 4H), 2.13-2.01 (m, 2H), 2.01-1.93 (m, J=6.9, 2H), 1.93-1.84 (m, 2H), 1.76-1.60 (m, 2H).

Workup

  1. customPrepared
  2. customfor 100 minutes

Sources & evidence

ORD record
ord-614841444e6942ed8883c698ab9f0b97
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

Loading…