Diisopropylethylamine → 3-Carbamoylmethoxy-N-[1-(2,6-diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-yl]-5-methoxy-benzamide

HRID 502462Notes

Reaction equation

HRID 502462 reaction equation
Cl.[C:2]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])(=[O:4])[NH2:3].[CH2:24]([O:26][C:27]1[CH:32]=[C:31]([CH:33]=O)[CH:30]=[C:29]([O:35][CH2:36][CH3:37])[C:28]=1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[CH3:25].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[C:2]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:10]([NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:33][C:31]2[CH:30]=[C:29]([O:35][CH2:36][CH3:37])[C:28]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:27]([O:26][CH2:24][CH3:25])[CH:32]=2)[CH2:17][CH2:18]1)=[O:11])(=[O:4])[NH2:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 593831002,6-Diethoxy-4'-fluoro-biphenyl-4-carbaldehydeHCID 68458066HCID 68458066, compound

Product 1

HCID 684582923-Carbamoylmethoxy-N-[1-(2,6-diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-yl]-5-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 3-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride (example 250b) was reacted with 2,6-diethoxy-4′-fluoro-biphenyl-4-carbaldehyde (example 102), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 580.2 (MH+).

Sources & evidence

ORD record
ord-d3be4e956c91484cb8e568ebd509376a
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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