Cyclohexane, (bromomethyl)- → 2-Tert-butoxy-2-[1-(cyclohexylmethyl)-6-methyl-4-(5-methylchroman-6-yl)-7-oxo-pyrrolo[2,3-c]pyridin-5-yl]acetic acid
Reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[NH:19][CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[C:23]([CH3:32])=[C:24]2[C:29](=[CH:30][CH:31]=1)[O:28][CH2:27][CH2:26][CH2:25]2)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[N:19]([CH2:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[C:23]([CH3:32])=[C:24]2[C:29](=[CH:30][CH:31]=1)[O:28][CH2:27][CH2:26][CH2:25]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared in a manner similar to that described in Example 49 step D from methyl 2-(tert-butoxy)-2-(6-methyl-4-(5-methylchroman-6-yl)-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and (bromomethyl)cyclohexane, and was isolated as white solid after reverse phase chromatography (45%): 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.35-7.28 (m, 0.4H), 6.99 (d, J=8.4 Hz, 0.6H), 6.90 (t, J=2.5 Hz, 1H), 6.78-6.67 (m, 1H), 5.73 (d, J=2.7 Hz, 0.4H), 5.67 (d, J=2.7 Hz, 0.6H), 5.40 (s, 0.4H), 5.15 (d, J=2.1 Hz, 0.6H), 4.48-4.34 (m, 1H), 4.34-4.23 (m, 1H), 4.23-4.12 (m, 2H), 3.73-3.61 (m, 3H), 2.79-2.57 (m, 2H), 2.16-2.05 (m, 2H), 2.05-1.98 (m, 2H), 1.98-1.83 (m, 2H), 1.75-1.55 (m, 5H), 1.40-0.91 (m, 14H); LCMS (m/z) ES+=521 (M+1).
Workup
- customwas isolated as white solid after reverse phase chromatography (45%)
Sources & evidence
- ORD record
- ord-a0129ec085914af88a3fa0a17ff82bc9
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012642B2
Reaction notes
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