Diisopropylethylamine → 3-(Methylcarbamoyl)isoxazol-5-ylmethyl 7-[5-(4-fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-ylcarbamate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:23][CH2:22][C:17]4([CH2:20][CH:19]([NH2:21])[CH2:18]4)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:24](=O)([O:36]C1C=CC([N+]([O-])=O)=CC=1)[O:25][CH2:26][C:27]1[O:31][N:30]=[C:29]([C:32](=[O:35])[NH:33][CH3:34])[CH:28]=1.C(N(CC)C(C)C)(C)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:23][CH2:22][C:17]4([CH2:18][CH:19]([NH:21][C:24](=[O:36])[O:25][CH2:26][C:27]5[O:31][N:30]=[C:29]([C:32](=[O:35])[NH:33][CH3:34])[CH:28]=5)[CH2:20]4)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1Participants
4
Reactant 3
Product 1
Procedure
The process is performed according to the procedure described in Example 1, step 1.1. Starting with 1.08 g (3.47 mmol) of 7-[5-(4-fluorophenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-ylamine, described in the preceding step (step 10.5.), 1.34 g (4.16 mmol) of 3-(methylcarbamoyl)isoxazol-5-ylmethyl 4-nitrophenyl carbonate, obtained in step 4.1., 1.12 g (8.67 mmol) of N,N-diisopropylethylamine and 0.212 g (1.73 mmol) of N,N-dimethylaminopyridine, and after purification by chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, 0.847 g of pure product is thus obtained in the form of a white solid.
Workup
- customobtained in step 4.1
- washeluting with a 98/2 mixture of dichloromethane and methanol, 0.847 g of pure product
- customis thus obtained in the form of a white solid
Sources & evidence
- ORD record
- ord-8db8295e527b436f9c94900238770981
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889702B2
Reaction notes
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