2-Methoxyethylamine → [(S)-4-Bromo-9-(2-methoxy-ethyl)-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohepta[e]inden-7-yl]-acetic acid methyl ester

HRID 132233Notes

Reaction equation

HRID 132233 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17]C)=O)[C:5]([CH2:11]Cl)=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[CH3:24][O:25][CH2:26][CH2:27][NH2:28].COC(=O)C[C@H]1C(=O)N(CC2CC2)CC2C3C=NNC=3C(Br)=CC=2C1>>[CH3:23][O:22][C:20](=[O:21])[CH2:19][C@H:14]1[C:15](=[O:17])[N:28]([CH2:27][CH2:26][O:25][CH3:24])[CH2:11][C:5]2[C:6]3[CH:7]=[N:8][NH:9][C:10]=3[C:2]([Br:1])=[CH:3][C:4]=2[CH2:13]1

Participants

4

Reactant 3

HCID 80182-MethoxyethylamineHCID 59731925((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acid methyl esterHCID 59732029(S)-dimethyl 2-((7-bromo-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate

Product 1

HCID 59731960[(S)-4-Bromo-9-(2-methoxy-ethyl)-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohepta[e]inden-7-yl]-acetic acid methyl esterYield 66%

Procedure

(S)-dimethyl 2-((7-bromo-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate (400 mg, 0.99 mmol) and 2-methoxyethylamine were reacted in a manner analogous to the preparation of ((S)-4-Bromo-9-cyclopropylmethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohept[e]inden-7-yl)-acetic acid methyl ester. Title compound was obtained as tan solid in 66% yield. MS m/e (M−H)−=408.1, 410.0.

Sources & evidence

ORD record
ord-b3a3f94849d4467d8f9af8bb9250380a
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

Loading…