Acetonitrile → Trifluoroacetic acid

HRID 1994444Notes

Reaction equation

HRID 1994444 reaction equation
C(N(CC)C(C1C=CC2N(C3CC4N(C)C(CC4)C3)C3C(OC=2C=1)=CC=CC=3)=O)C.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32].[CH2:38]([N:40]([CH2:75][CH3:76])[C:41]([C:43]1[CH:44]=[CH:45][C:46]2[N:47]([CH:59]3[CH2:65][CH:64]4[N:66]([CH2:67]CC5C=CC=CC=5)[CH:61]([CH2:62][CH2:63]4)[CH2:60]3)[C:48]3[C:53]([O:54][C:55]=2[CH:56]=1)=[C:52]([O:57][CH3:58])[CH:51]=[CH:50][CH:49]=3)=[O:42])[CH3:39].C(#N)C>O>[CH2:75]([N:40]([CH2:38][CH3:39])[C:41]([C:43]1[CH:44]=[CH:45][C:46]2[N:47]([CH:59]3[CH2:60][CH:61]4[N:66]([CH3:67])[CH:64]([CH2:63][CH2:62]4)[CH2:65]3)[C:48]3[C:53]([O:54][C:55]=2[CH:56]=1)=[C:52]([O:57][CH3:58])[CH:51]=[CH:50][CH:49]=3)=[O:42])[CH3:76].[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 116709266-methoxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide2×HCID 1169711110-(8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide2×

Product 2

HCID 6422Trifluoroacetic acidHCID 117190476-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using an adaptation of Procedure 16, and substituting the TFA salt of 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 4e for TFA salt of 6-methoxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 6e, the title compound 6-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 8e was obtained as a TFA salt and as a mixture of endo and exo isomers after reverse phase chromatography (eluent gradient: acetonitrile in water containing 0.1% TFA). MS m/z (MH+) 422.

Sources & evidence

ORD record
ord-c4ab166890f84419991b5a59d0430f6d
Source dataset
uspto-grants-2010_01
Patent number
US07652005B2

Reaction notes

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