Trichloroacetyl chloride → HCID 58727969, compound

HRID 1992187Notes

Reaction equation

[NH2:1][C:2]([CH2:40][CH3:41])([CH2:38][CH3:39])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)([CH2:11][CH2:12][N:13]2[CH:18]3[CH2:19][CH2:20][CH:14]2[CH2:15][CH:16]([N:21]2[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]2[CH3:30])[CH2:17]3)[CH2:7][CH2:6]1)=[O:4].[Cl:42][C:43]([Cl:48])([Cl:47])[C:44](Cl)=[O:45].CCN(C(C)C)C(C)C>>[Cl:42][C:43]([Cl:48])([Cl:47])[C:44]([NH:1][C:2]([CH2:40][CH3:41])([C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)([CH2:11][CH2:12][N:13]2[C@H:18]3[CH2:19][CH2:20][C@@H:14]2[CH2:15][CH:16]([N:21]2[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]2[CH3:30])[CH2:17]3)[CH2:7][CH2:6]1)=[O:4])[CH2:38][CH3:39])=[O:45]

Participants

Reactant 3

HCID 6420Trichloroacetyl chloride

HCID 81531Diisopropylethylamine

HCID 58727859HCID 58727859, compound

Product 1

HCID 58727969HCID 58727969, compoundYield 54.2%

Procedure

2-Amino-2-ethyl-1-(4-(3-fluoro-phenyl)-4-{2-[3-(2-methyl-benzoimidazol-1-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-ethyl}-piperidin-1-yl)-butan-1-one (0.100 g, 0.178 mmol), trichloroacetyl chloride (0.032 g, 0.178 mmol) and DIEA (0.069 g, 0.534 mmol) as outlined in procedure for procedure for Example 890 to give title compound, 2,2,2-trichloro-N-{1-ethyl-1-[(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]propyl}acetamide (0.068 g, 54%). ES-LCMS m/z 706 (M+1).

Sources & evidence

ORD record: ord-464515840eb34aeca0a611d8dc445ebc
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645771B2

Reaction notes

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