Trifluoroacetic acid → Trifluoroacetic acid

HRID 2114510Notes

Reaction equation

HRID 2114510 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[NH:27][C:28](=[O:30])[CH3:29])=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:3][CH2:2]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32].N1CCC([N:44]2[C:57]3[CH:56]=CC(C4NN=NN=4)=CC=3O[C:50]3[C:45]2=CC=CC=3)CC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].C[N+:79](C)(C)C>ClCCCl.C1COCC1>[NH:44]1[CH:57]=[CH:56][N:79]=[C:45]1[CH2:50][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[NH:27][C:28](=[O:30])[CH3:29])=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][CH2:6]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 28122N,N,N-Trimethylmethanaminium tetrahydroborateHCID 5049666Sodium triacetoxyborohydrideHCID 11711042HCID 11711042, compoundHCID 178419906HCID 178419906, compound2×

Product 2

HCID 6422Trifluoroacetic acidHCID 11719932HCID 11719932, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Using an adaptation of the method described in Procedure 7, substituting N-[2-(10-piperidin-4-yl-10H-phenoxazin-3-yl)-phenyl]-acetamide, 2j for the TFA salt of 10-piperidin-4-yl-3-(1H-tetrazol-5-yl)-10H-phenoxazine, 6a, sodium triacetoxyborohydride for tetramethylammonium borohydride, and a 3:1 mixture of 1,2-dichloroethane:THF for 100% 1,2-dichloroethane, the title compound N-(2-{10-[1-(1H-imidazol-2-ylmethyl)-piperidin-4-yl]-10H-phenoxazin-3-yl}-phenyl)-acetamide, 7j was obtained as a TFA salt after purification via reverse phase HPLC (eluent: CH3CN in H2O containing 0.1% TFA). MS m/z (MH+) 479.9.

Sources & evidence

ORD record
ord-fc6795bdaa284192a9db13338bbb28e9
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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