Trifluoroacetic acid → HCID 178419907, compound

HRID 2114490Notes

Reaction equation

C(O)(C(F)(F)F)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]1.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClC(Cl)C>[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH2:38][N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the TFA salt of 10-piperidin-4-yl-3-(1H-tetrazol-5-yl)-10H-phenoxazine, 6a (40.7 mg; 0.091 mmol) and 1H-imidazole-2-carboxaldehyde (35 mg; 0.36 mmol) in dichloroethane (5 mL) was added tetramethylammonium triacetoxyborohydride (36 mg; 0.14 mmol). The mixture was heated to 80° C. for 15 hr in a sealed tube. The mixture was allowed to cool to rt, and the solvent was removed via evaporation. The residue was purified via reverse phase HPLC (eluent gradient: 15 to 40% acetonitrile in water containing 0.1% TFA) to yield 3.1 mg (6.5%) of 10-[1-(1H-imidazol-2-ylmethyl)-piperidin-4-yl]-3-(1H-tetrazol-5-yl)-10H-phenoxazine, 7a as a TFA salt. MS m/z (MH+) 414.9.

Workup

temperatureto cool to rt
customthe solvent was removed via evaporation
customThe residue was purified via reverse phase HPLC (eluent gradient: 15 to 40% acetonitrile in water containing 0.1% TFA)

Sources & evidence

ORD record: ord-f01acd927de24e888115af4edd248fdc
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432257B2

Reaction notes

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