2-chloro-N,N-diethyl-4-methylbenzamide → HCID 11659097, compound

HRID 2100601Notes

Reaction equation

HRID 2100601 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]([CH3:23])[CH:3]=1.ClC1C=C(C)C=CC=1C(N(CC)CC)=O>>[ClH:1].[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][C@@H:8]3[CH2:13][NH:14][CH2:15][C@H:7]3[C:6]=2[CH:5]=[C:4]([CH3:23])[CH:3]=1

Participants

3

Reactant 2

HCID 8858472-chloro-N,N-diethyl-4-methylbenzamideHCID 69053755HCID 69053755, compound

Product 1

HCID 11659097HCID 11659097, compound

Procedure

Following the procedure described in Example 23, Part K, (3aS,9bR)-tert-butyl 6-chloro-5-oxo-8-methyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the second eluting compound from Example 37, Part C, was converted into the title compound of Example 38 as an off-white solid. 1H NMR (DMSO-D6): δ 9.55 (broad s, 1H), 9.41 (broad s, 1H), 8.67 (s, 1H), 7.29 (s, 1H), 7.02 (s, 1H), 3.85-3.80 (m, 1H), 3.66-3.61 (m, 1H), 3.58-3.52 (m, 1H), 3.30-3.25 (m, 1H), 3.15-3.10 (m, 1H), 3.07-3.02 (m, 1H), 2.30 (s, 3H). LRMS (ESI): 237.1/239.1 (M+H)+.

Sources & evidence

ORD record
ord-a1b9a2006e894cbf9e5183908e5cb4cd
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…