Dimethylamine → (3aSR,10RS)-6-(1,1-Difluoro-methoxy)-2-(2-dimethylamino-ethyl)-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

HRID 41038Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[C:30](=[O:31])[N:7]2[CH:8]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][C:6]2([CH3:32])[C:5]1=[O:33])=[CH:15][C:14]([O:19][CH:20]([F:22])[F:21])=[CH:13][CH:12]=4.[CH3:34][NH:35][CH3:36]>>[F:22][CH:20]([F:21])[O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]1[CH:8]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)[N:7]3[C:30](=[O:31])[N:4]([CH2:3][CH2:2][N:35]([CH3:36])[CH3:34])[C:5](=[O:33])[C:6]3([CH3:32])[CH2:18][C:17]2=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 68939720(3aSR,10RS)-2-(2-Bromoethyl)-6-(1,1-difluoro-methoxy)-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

Product 1

HCID 68941772(3aSR,10RS)-6-(1,1-Difluoro-methoxy)-2-(2-dimethylamino-ethyl)-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

Procedure

The title compound is prepared similarly as described for example 29 using (3aSR,10RS)-2-(2-Bromoethyl)-6-(1,1-difluoro-methoxy)-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione (example 36) and dimethyl amine instead of azetidine as starting materials. MS: m/z (MH+)=485.2

Sources & evidence

ORD record: ord-f381c597ed824e8a910b25ba41fdfa89
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530493B2

Reaction notes

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