Acetic Acid → HCID 178489345, compound

HRID 2196571Notes

Reaction equation

HRID 2196571 reaction equation
[CH3:1][N:2]([CH2:10][CH:11]=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[NH:25][C:24]2[C:26]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:27][CH:28]=[CH:29][C:23]=2[N:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[NH:25][C:24]2[C:26]([CH:30]3[CH2:35][CH2:34][N:33]([CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH2:32][CH2:31]3)=[CH:27][CH:28]=[CH:29][C:23]=2[N:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 178489344HCID 178489344, compound

Product 1

HCID 178489345HCID 178489345, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl methyl(2-oxoethyl)carbamate (0.165 g, 0.950 mmol) in DCM (3 ml) was added a solution of 175 (0.292 g, 0.950 mmol) in MeOH (3.00 ml) followed by acetic acid (0.082 ml, 1.425 mmol) and after 1 hour of stirring at room temperature, sodium triacetoxyborohydride (0.242 g, 1.140 mmol) was added according to the procedure described for 59 (scheme 8, example 6, step 7) to give tert-butyl 2-(4-(2-(2-methoxyphenyl)-1H-benzo[d]imidazol-7-yl)piperidin-1-yl)ethyl(methyl)-carbamate (0.114 g, 0.245 mmol, 25.8% yield) as a white crusty solid. LRMS (ESI): (calc.) 464.6 (found) 465.5 (MH)+

Sources & evidence

ORD record
ord-4bff9553308246298b8241f533354153
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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