Morpholine → 4-(3-(1-((4iodo-5-methyl-1H-pyrazol-1-yl)methyl)cycloheptyloxy)propyl)morpholine
Reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:16][CH2:17][CH2:18][CH:19]=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]=1[CH3:7].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:16][CH2:17][CH2:18][CH2:19][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:6]=1[CH3:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of EXAMPLE 155C (393 mg) in dichloromethane (20 mL) was added morpholine (263 mg) and sodium triacetoxyborohydride (427 mg). After the reaction mixture was stirred overnight at room temperature, 2N NaOH aqueous solution (10 mL) was added and the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and a saturated NaCl solution. After the organic layer was dried over Na2SO4, it was filtered and the solvent was evaporated under reduced pressure. The crude product was used in the next reaction without further purification.
Workup
- extractionthe reaction mixture was extracted with ethyl acetate
- washthe organic layer was washed with water
- dry with materialAfter the organic layer was dried over Na2SO4, it
- filtrationwas filtered
- customthe solvent was evaporated under reduced pressure
- customThe crude product was used in the next reaction without further purification
Sources & evidence
- ORD record
- ord-88a4910fcc1744df9addd8bf2befe1c8
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940737B2
Reaction notes
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