2-(3-Bromopropoxy)tetrahydro-2H-pyran → HCID 17854368, compound

HRID 218761Notes

Reaction equation

HRID 218761 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=1)[CH2:22][C:23]1[CH:24]=[N:25][NH:26][CH:27]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:38][CH2:39][CH2:40][O:41][CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][O:43]1>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([C:28]1[CH:29]=[CH:30][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:32][CH:33]=1)[CH2:22][C:23]1[CH:27]=[N:26][N:25]([CH2:38][CH2:39][CH2:40][O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)[CH:24]=1)=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 178542505-benzyloxy-N-(4-isopropylphenyl)-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide

Product 1

HCID 17854368HCID 17854368, compound

Procedure

By the reaction and treatment in the same manner as in Example 83 using 5-benzyloxy-N-(4-isopropylphenyl)-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (1.02 g) and 1-bromo-3-(2-oxanyloxy)propane (0.45 mL) as starting materials, 5-benzyloxy-N-(4-isopropylphenyl)-N-({1-[3-(2-oxanyloxy)propyl]pyrazol-4-yl}methyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (1.65 g) was obtained. This compound was dissolved in methanol (30 mL), and 4 mol/L-HCl/dioxane (0.1 mL) was added. The mixture was stirred at room temperature for 2 hr. Into the reaction mixture was poured saturated aqueous sodium hydrogencarbonate (2 mL). The reaction mixture was concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated. By the reaction and treatment of the obtained residue (0.94 g) in the same manner as in Example 105, 5-hydroxy-N-{[1-(3-hydroxypropyl)pyrazol-4-yl]methyl}-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.58 g) was obtained.

Sources & evidence

ORD record
ord-34275b037ede4270a2d60065a3230318
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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