Diisopropylethylamine → Rac-n-[1-(3,5-diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-yl]-3-(2,3-dihydroxy-propoxy)-5-methoxy-benzamide

HRID 502439Notes

Reaction equation

HRID 502439 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH:9]([CH2:29][OH:30])[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[C:15]([NH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:16].[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([CH:39]=[C:40]([O:47][CH2:48][CH3:49])[C:41]=1[N:42]1[CH:46]=[CH:45][CH:44]=[CH:43]1)[CH:37]=O)[CH3:32].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([CH:39]=[C:40]([O:47][CH2:48][CH3:49])[C:41]=1[N:42]1[CH:46]=[CH:45][CH:44]=[CH:43]1)[CH2:37][N:21]1[CH2:22][CH2:23][CH:18]([NH:17][C:15](=[O:16])[C:14]2[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:12]([O:11][CH2:10][CH:9]([OH:8])[CH2:29][OH:30])[CH:13]=2)[CH2:19][CH2:20]1)[CH3:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehydeHCID 68458548rac-3-(2,3-Dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide trifluoroacetate

Product 1

HCID 68457845Rac-n-[1-(3,5-diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-yl]-3-(2,3-dihydroxy-propoxy)-5-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), crude rac-3-(2,3-dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide trifluoroacetate (example 175b) was reacted with 3,5-diethoxy-4-pyrrol-1-yl-benzaldehyde (example 40b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as yellow oil. MS: 568.5 (MH+).

Sources & evidence

ORD record
ord-3f0a707d047d4a9096829ba360562778
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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