Azetidine hydrochloride → 3-(2-(Azetidin-1-yl)pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4,3-c]pyridine

HRID 1046499Notes

Reaction equation

HRID 1046499 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.[NH:44]1[CH2:47][CH2:46][CH2:45]1>>[N:44]1([C:2]2[CH:7]=[C:6]([C:8]3[C:12]4[C:13]([O:17][CH:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)=[N:14][CH:15]=[CH:16][C:11]=4[NH:10][N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:47][CH2:46][CH2:45]1

Participants

3

Reactant 2

HCID 12308726Azetidine hydrochlorideHCID 866736963-(2-Chloropyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 668291713-(2-(Azetidin-1-yl)pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4,3-c]pyridineYield 22%

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 azetidine hydrochloride to give the title compound (11.3 mg, 22% over two steps). LC-MS (Method G): m/z=352.1 [M+H]+; 3.24 min. 1H-NMR (400 MHz, DMSO): δ 13.72 (s, 1H), 8.17-8.11 (m, 1H), 7.91 (d, J=5.6, 1H), 7.29-7.22 (m, 1H), 7.17 (d, J=5.6, 1H), 6.93 (s, 1H), 5.56-5.46 (m, 1H), 4.09-3.95 (m, 4H), 3.85-3.75 (m, 2H), 3.58-3.48 (m, 2H), 2.41-2.31 (m, 2H), 2.11-2.01 (m, 2H), 1.77-1.63 (m, 2H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9c93a9c4dd854f0c9f5cf04031ae4bfd
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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