Pivaloyl chloride → HCID 68679108, compound

HRID 1992162Notes

Reaction equation

[NH2:1][CH:2]([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].[CH3:40][C:41]([CH3:46])([CH3:45])[C:42](Cl)=[O:43].CCN(C(C)C)C(C)C>>[F:37][C:33]1[CH:32]=[C:31]([C:8]2([CH2:11][CH2:12][N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH2:15][CH:16]([N:21]3[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[N:23]=[C:22]3[CH3:30])[CH2:17]4)[CH2:9][CH2:10][N:5]([C:3]([CH:2]([NH:1][C:42](=[O:43])[C:41]([CH3:46])([CH3:45])[CH3:40])[CH2:38][CH3:39])=[O:4])[CH2:6][CH2:7]2)[CH:36]=[CH:35][CH:34]=1

Participants

Reactant 3

HCID 62493Pivaloyl chloride

HCID 81531Diisopropylethylamine

HCID 68677086HCID 68677086, compound

Product 1

HCID 68679108HCID 68679108, compoundYield 54%

Procedure

N-[1-(4-(3-Fluoro-phenyl)-4-{2-[3-(2-methyl-benzoimidazol-1-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-ethyl}-piperidine-1-carbonyl)-propyl]-2,2-dimethyl-propionamide was obtained from treating[1-(4-(3-Fluoro-phenyl)-4-{2-[3-(2-methyl-benzoimidazol-1-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-ethyl}-piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester (0.580 g, 0.92 mmol) with HCl as outlined in the procedure for example 890 to form 2-Amino-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 (0.488 g, 99%). 2-Amino-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 (0.049 g, 0.09 mmol, 2,2-Dimethyl-propionyl chloride (0.011 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, N-[1-(4-(3-Fluoro-phenyl)-4-{2-[3-(2-methyl-benzoimidazol-1-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-ethyl}-piperidine-1-carbonyl)-propyl]-2,2-dimethyl-propionamide (0.030 g, 54%) as an oil. ES-LCMS m/z 616 (M+1).

Sources & evidence

ORD record: ord-018e176961554c73bc5f07c0c7e0d94a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645771B2

Reaction notes

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