Hydrochloric Acid → HCID 68677313, compound

HRID 1992170Notes

Reaction equation

HRID 1992170 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:28][CH2:29][N:30]3[C@H:35]4[CH2:36][CH2:37][C@@H:31]3[CH2:32][CH:33]([N:38]3[C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=5[N:40]=[C:39]3[CH3:47])[CH2:34]4)[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3C(OC(C)(C)C)=O)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:28][CH2:29][N:30]3[C@H:35]4[CH2:36][CH2:37][C@@H:31]3[CH2:32][CH:33]([N:38]3[C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=5[N:40]=[C:39]3[CH3:47])[CH2:34]4)[CH2:13][CH2:12][N:11]([C:14](=[O:15])[C@@H:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58727933HCID 58727933, compound

Product 1

HCID 68677313HCID 68677313, compoundYield 99.2%

Procedure

1-[(1R,5S)-8-(2-{4-(3-fluorophenyl)-1-[1-(trifluoroacetyl)-L-prolyl]-4-piperidinyl}ethyl)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole was obtained from treating 1,1-dimethylethyl (2S)-2-[(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-1-piperidinyl)carbonyl]-1-pyrrolidinecarboxylate (0.645 g, 1.01 mmol) with HCl as outlined in the procedure for Example 890 to form 1-((1R,5S)-8-{2-[4-(3-fluorophenyl)-1-L-prolyl-4-piperidinyl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole (0.545 g, 99%). 1-((1R,5S)-8-{2-[4-(3-fluorophenyl)-1-L-prolyl-4-piperidinyl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole (0.050 g, 0.09 mmol), trifluoroaceticanhydirde (0.019 g, 0.09 mmol) and DIEA (0.034 g, 0.534 mmol) were reacted following the procedure outlined in Example 890 to give the title compound, 1-[(1R,5S)-8-(2-{4-(3-fluorophenyl)-1-[1-(trifluoroacetyl)-L-prolyl]-4-piperidinyl}ethyl)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole (0.021 g, 36%) as an oil. ES-LCMS m/z 640 (M+1).

Sources & evidence

ORD record
ord-f8111b6922cd47be9a1a04fee7bfe8d0
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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