Diisopropylethylamine → N-[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-yl]-3-(2H-tetrazol-5-yl)-benzamide

HRID 502443Notes

Reaction equation

HRID 502443 reaction equation
C(OC1C=C(C=C(OCC)C=1F)C[N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:27])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[N:23]=[N:24][NH:25][N:26]=3)[CH:17]=2)[CH2:10][CH2:9]1)C.[CH:35]([O:38][C:39]1[CH:40]=[C:41]([CH:44]=[C:45]([O:47][CH:48]([CH3:50])[CH3:49])[CH:46]=1)[CH:42]=O)([CH3:37])[CH3:36].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH:35]([O:38][C:39]1[CH:40]=[C:41]([CH:44]=[C:45]([O:47][CH:48]([CH3:50])[CH3:49])[CH:46]=1)[CH2:42][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:27])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[N:23]=[N:24][NH:25][N:26]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 113106053,5-DiisopropoxybenzaldehydeHCID 68456697N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-(2H-tetrazol-5-yl)-benzamide

Product 1

HCID 68459127N-[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-yl]-3-(2H-tetrazol-5-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), N-piperidin-4-yl-3-(1H-tetrazol-5-yl)-benzamide (example 178) was reacted with 3,5-diisopropoxy-benzaldehyde (example 126b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 479.3 (MH+).

Sources & evidence

ORD record
ord-4da1d6d071d845e2a16153a677f2d9ad
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

Loading…