Trifluoroacetic acid → Trifluoroacetic acid

HRID 1994449Notes

Reaction equation

HRID 1994449 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C[O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[NH:18][CH:19]1[CH2:25][CH:24]2[N:26]([CH3:27])[CH:21]([CH2:22][CH2:23]2)[CH2:20]1)[C:13]#[N:14].C(N(CC)C(C1C=CC2N(C3CC4N(CCC5C=CC=CC=5)C(CC4)C3)C3C(OC=2C=1)=C(OC)C=CC=3)=O)C>>[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[NH:18][CH:19]1[CH2:25][CH:24]2[N:26]([CH3:27])[CH:21]([CH2:22][CH2:23]2)[CH2:20]1)[C:13]#[N:14].[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 116709266-methoxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide2×HCID 598147413-Methoxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile2×

Product 2

HCID 6422Trifluoroacetic acidHCID 598146983-Hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile

Procedure

Using an adaptation of Procedure 13, substituting the TFA salt of 3-methoxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile, 1p for the 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 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile, 2p was obtained as TFA salt and as a mixture of endo and exo isomers after purification via reverse phase HPLC (eluent gradient: 20% to 45% CH3CN in water containing 0.1% TFA). MS m/z=258 (M+1).

Sources & evidence

ORD record
ord-ab4f4e57b3d646afae702a37e5b051ab
Source dataset
uspto-grants-2010_01
Patent number
US07652005B2

Reaction notes

Loading…