Oxetane, 3-(bromomethyl)-3-methyl- → 4-Methoxy-3-(1-((3-methyloxetan-3-yl)methyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 1046492Notes

Reaction equation

HRID 1046492 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:31]3[CH:32]=[N:33][NH:34][CH:35]=3)=[N:10][N:11](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:7]=2[CH:6]=[CH:5][N:4]=1.Br[CH2:37][C:38]1([CH3:42])[CH2:41][O:40][CH2:39]1>>[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:31]3[CH:35]=[N:34][N:33]([CH2:37][C:38]4([CH3:42])[CH2:41][O:40][CH2:39]4)[CH:32]=3)=[N:10][NH:11][C:7]=2[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 144860Oxetane, 3-(bromomethyl)-3-methyl-HCID 136352321HCID 136352321, compound

Product 1

HCID 569420804-Methoxy-3-(1-((3-methyloxetan-3-yl)methyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 35%

Procedure

Prepared according to the general procedure described in Example 86, by reacting 4-methoxy-3-(1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine with 3-(bromomethyl)-3-methyloxetane to give the title compound (23.1 mg, 35% over two steps). LC-MS (Method G): m/z=300.0 [M+H]+; 2.54 min. 1H-NMR (400 MHz, DMSO) δ 8.75 (s, 2H), 7.47 (d, J=5.8, 1H), 7.00 (d, J=6.0, 1H), 4.54 (d, J=11.7, 2H), 4.31 (d, J=11.8, 2H), 4.01 (s, 2H), 3.50 (s, 5H), 1.31 (s, 3H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-08db81c6f8054fcc803281132fb8438e
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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