Tert-butyl (S)-3-(((5-(ethylsulfonyl)pyridin-2-yl)methyl)carbamoyl)-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate → (S)-N-((5-(ethylsulfonyl)pyridin-2-yl)methyl)-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxamide
Reaction equation
C(S(C1C=CC(CNC(C2C=C3CN[C@@H](C(C)C)C3=NC=2)=O)=CC=1)(=O)=O)C.[CH2:28]([S:30]([C:33]1[CH:34]=[CH:35][C:36]([CH2:39][NH:40][C:41]([C:43]2[CH:44]=[C:45]3[CH2:51][N:50](C(OC(C)(C)C)=O)[C@@H:49]([CH:59]([CH3:61])[CH3:60])[C:46]3=[N:47][CH:48]=2)=[O:42])=[N:37][CH:38]=1)(=[O:32])=[O:31])[CH3:29]>>[CH2:28]([S:30]([C:33]1[CH:34]=[CH:35][C:36]([CH2:39][NH:40][C:41]([C:43]2[CH:44]=[C:45]3[CH2:51][NH:50][C@@H:49]([CH:59]([CH3:60])[CH3:61])[C:46]3=[N:47][CH:48]=2)=[O:42])=[N:37][CH:38]=1)(=[O:31])=[O:32])[CH3:29]Participants
3
Reactant 2
Product 1
Procedure
Procedure same as that for (S)-N-(4-(ethylsulfonyl)benzyl)-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxamide, using tert-butyl(S)-3-(((5-(ethylsulfonyl)pyridin-2-yl)methyl)carbamoyl)-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate as a starting material. LC-MS tR=0.48 min in 1 min chromatography, MS (ESI) m/z 389.3 [M+H]+. 1H NMR (CDCl3, 400 MHz): δ 9.06 (dd, J=0.8 Hz, 2.0 Hz, 1H), 8.93 (t, J=0.8 Hz, 1H), 8.19 (dd, J=2.0 Hz, 8.4 Hz, 1H), 8.01 (t, J=0.8 Hz, 1H), 7.56 (dd, J=0.8 Hz, 8.0 Hz, 1H), 7.52 (s, 1H), 4.89 (d, J=5.2 Hz, 2H), 4.35 (dd, J=1.2 Hz, 4.0 Hz, 1H), 4.32 (d, J=0.8 Hz, 2H), 3.17 (q, J=7.6 Hz, 2H), 2.34-2.26 (m, 1H), 1.33 (t, J=7.6 Hz, 3H), 1.09 (d, J=7.2 Hz, 3H), 0.79 (d, J=6.8 Hz, 3H).
Sources & evidence
- ORD record
- ord-c47eac69d6e24125b2963d34554526c3
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266886B2
Reaction notes
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