9-(8-Aza-bicyclo[3.2.1]oct-3-ylidene)-5-bromo-9H-xanthene-3-carboxylic acid diethylamide → Trifluoroacetic acid

HRID 733403Notes

Reaction equation

HRID 733403 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:21]3[CH2:27][CH:26]4[N:28]([C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[CH:23]([CH2:24][CH2:25]4)[CH2:22]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[C:13]([F:20])[CH:12]=3)=[O:5])[CH3:2].C(N(CC)C(C1C=CC2C(=C3CC4N(C(=O)C(F)(F)F)C(CC4)C3)C3C(OC=2C=1)=C(OC)C=CC=3)=[O:41])C.C(N(CC)C(C1C=CC2C(=C3CC4NC(CC4)C3)C3C(OC=2C=1)=C(Br)C=CC=3)=O)C>>[CH2:35]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:21]3[CH2:27][CH:26]4[NH:28][CH:23]([CH2:24][CH2:25]4)[CH2:22]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[C:13]([F:20])[CH:12]=3)=[O:5])[CH3:36].[C:29]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:41]

Participants

5

Reactant 3

HCID 469179409-(8-Aza-bicyclo[3.2.1]oct-3-ylidene)-5-bromo-9H-xanthene-3-carboxylic acid diethylamideHCID 578392497-Fluoro-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carboxylic acid diethylamideHCID 578392625-Methoxy-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carboxylic acid diethylamide

Product 2

HCID 6422Trifluoroacetic acidHCID 113043189-(8-Aza-bicyclo[3.2.1]oct-3-ylidene)-7-fluoro-9H-xanthene-3-carboxylic acid diethylamide

Procedure

Using an adaptation of the method described in Procedure 17, substituting 7-fluoro-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carboxylic acid diethylamide, 5e for 5-methoxy-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carboxylic acid diethylamide, 5d, the title compound 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-7-fluoro-9H-xanthene-3-carboxylic acid diethylamide, 6e was obtained as TFA salt after reverse phase HPLC purification (eluent gradient: CH3CN in H2O containing 0.1% TFA). MS m/z (MH+) 407.1.

Sources & evidence

ORD record
ord-ff6013232eb14545bc366b0a3461919d
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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