4-(Bromomethyl)oxane → 2-Tert-butoxy-2-[6-methyl-4-(5-methylchroman-6-yl)-7-oxo-1-(tetrahydropyran-4-ylmethyl)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][O: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][O: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 4-(bromomethyl)tetrahydro-2H-pyran, and was isolated as beige solid after reverse phase chromatography (45%): 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.29 (d, J=8.6 Hz, 0.5H), 7.02-6.96 (m, 0.5H), 6.96-6.90 (m, 1H), 6.80-6.66 (m, 1H), 5.81-5.67 (m, 1H), 5.46-5.10 (m, 1H), 4.54-4.28 (m, 2H), 4.28-4.12 (m, 2H), 4.03-3.91 (m, 2H), 3.75-3.64 (m, 3H), 3.46-3.30 (m, 2H), 2.81-2.55 (m, 2H), 2.22 (d, J=3.7 Hz, 1H), 2.17-2.05 (m, 2H), 2.05-1.88 (m, 3H), 1.65-1.46 (m, 2H), 1.46-1.28 (m, 2H), 1.15 (s, 6H), 1.02 (s, 3H); LCMS (m/z) ES+=523 (M+1).
Workup
- customwas isolated as beige solid after reverse phase chromatography (45%)
Sources & evidence
- ORD record
- ord-eccb4d69445c4cb5b5dafa4bd87d9e8b
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012642B2
Reaction notes
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