N,N-Diethyl 4-bromo-2-chlorobenzamide → (3aS,9bR)-6-Chloro-4-methyl-8-propyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one hydrochloride

HRID 2100594Notes

Reaction equation

HRID 2100594 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][C@@H:8]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C@H:7]3[C:6]=2[CH:5]=[C:4]([CH2:23][CH2:24][CH3:25])[CH:3]=1.Br[C:27]1C=CC(C(N(CC)CC)=O)=C(Cl)C=1>>[ClH:1].[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:27])[C@@H:8]3[CH2:13][NH:14][CH2:15][C@H:7]3[C:6]=2[CH:5]=[C:4]([CH2:23][CH2:24][CH3:25])[CH:3]=1

Participants

3

Reactant 2

HCID 16115931N,N-Diethyl 4-bromo-2-chlorobenzamideHCID 69054733(3aS,9bR)-tert-butyl 6-chloro-5-oxo-8-propyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate

Product 1

HCID 11638235(3aS,9bR)-6-Chloro-4-methyl-8-propyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one hydrochloride

Procedure

Following the procedures described in Example 24, Parts A and B, (3aS,9bR)-tert-butyl 6-chloro-5-oxo-8-propyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the second eluting compound from Example 23, Part J, was converted to the title compound of Example 26 as an off-white solid. 1H NMR (DMSO-D6): δ 9.77 (broad s, 2H), 7.33 (s, 1H), 7.05 (s, 1H), 3.96-3.90 (m, 1H), 3.80-3.65 (overlapping m, 2H), 3.48-3.20 (overlapping m, 3H), 2.99 (s, 3H), 2.58 (t, 2H, J=7.7 Hz), 1.65-1.55 (m, 2H), 0.89 (t, 3H, J=7.3 Hz). LRMS (ESI): 279.09/281.07 (M+H)+.

Sources & evidence

ORD record
ord-8731983cf88048d99c84c879be0c2acc
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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