Trifluoroacetic acid → HCID 59809567, compound

HRID 2114496Notes

Reaction equation

HRID 2114496 reaction equation
[C:1]([OH:7])([C:3](F)(F)F)=[O:2].[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25]C(C4NN=NN=4)=[CH:23][C:22]=3[O:21]C3C2=CC=CC=3)[CH2:10][CH2:9]1.[CH2:33](N1CCC(=O)CC1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1C=CN=[C:48]1C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>>[CH3:48][O:7][C:1](=[O:2])[C:3]1[CH:25]=[CH:26][C:27]([NH:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:13][CH2:12]2)=[C:22]([OH:21])[CH:23]=1

Participants

7

Reactant 6

HCID 6422Trifluoroacetic acidHCID 192201-Benzyl-4-piperidoneHCID 249551H-imidazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 178419906HCID 178419906, compound2×

Product 1

HCID 59809567HCID 59809567, compound

Procedure

Using an adaptation of the method described in Procedure 7, substituting 4-amino-3-hydroxy-benzoic acid methyl ester for the TFA salt of 10-piperidin-4-yl-3-(1H-tetrazol-5-yl)-10H-phenoxazine, 6a, 1-benzyl-piperidin-4-one for 1H-imidazole-2-carboxaldehyde, and sodium triacetoxyborohydride for tetramethylammonium triacetoxyborohydride, the title compound 4-(1-benzyl-piperidin-4-ylamino)-3-hydroxy-benzoic acid methyl ester, 1d was obtained.

Sources & evidence

ORD record
ord-9facc24cab7449dbbe15b7cc518f8654
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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