Tert-butyl (S)-3-(2-(4-(ethylsulfonyl)phenyl)acetamido)-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate → (S)-2-(4-(ethylsulfonyl)phenyl)-N-(7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)acetamide

HRID 1777823Notes

Reaction equation

HRID 1777823 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:38]=[CH:37][C:36]([CH2:39][C:40]([NH:42][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:41])=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH3:29]>>[CH2:28]([S:30]([C:33]1[CH:34]=[CH:35][C:36]([CH2:39][C:40]([NH:42][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:41])=[CH:37][CH:38]=1)(=[O:32])=[O:31])[CH3:29]

Participants

3

Reactant 2

HCID 118274878Tert-butyl (S)-3-(2-(4-(ethylsulfonyl)phenyl)acetamido)-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylateHCID 118274972(S)N-(4-(ethylsulfonyl)benzyl)-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxamide

Product 1

HCID 118274927(S)-2-(4-(ethylsulfonyl)phenyl)-N-(7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)acetamide

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-(2-(4-(ethylsulfonyl)phenyl)acetamido)-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate as a starting material. LC-MS tR=0.50 min in 1 min chromatography, MS (ESI) m/z 388.3 [M+H]+. 1H NMR (CD3OD, 400 MHz): δ 9.02 (s, 1H), 8.48 (s, 1H), 8.26 (d, J=2.0 Hz, 1H), 7.84 (m, 2H), 7.66 (d, J=8.0 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 4.78 (m, 2H), 3.98 (s, 1H), 3.81 (s, 1H), 3.70 (s, 1H), 3.20 (q, J=7.6 Hz, 2H), 2.65-2.57 (m, 1H), 1.21 (t, J=7.6 Hz, 3H), 1.21 (d, J=6.8 Hz, 3H), 1.03 (d, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-9bc42ecccbda48c0ba8fd511c5fafd2b
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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