Diisopropylethylamine → 2-{3-[1-(3,5-Diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-2-methyl-propionic acid ethyl ester

HRID 502403Notes

Reaction equation

HRID 502403 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:8][C:9]1[CH:14]=[C:13]([C:15](=[O:23])[NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:12]=[C:11]([O:24][CH3:25])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[CH2:27]([O:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([O:43][CH2:44][CH3:45])[C:37]=1[N:38]1[CH:42]=[CH:41][CH:40]=[CH:39]1)[CH:33]=O)[CH3:28].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:8][C:9]1[CH:10]=[C:11]([O:24][CH3:25])[CH:12]=[C:13]([C:15](=[O:23])[NH:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:33][C:32]3[CH:35]=[C:36]([O:43][CH2:44][CH3:45])[C:37]([N:38]4[CH:42]=[CH:41][CH:40]=[CH:39]4)=[C:30]([O:29][CH2:27][CH3:28])[CH:31]=3)[CH2:21][CH2:22]2)[CH:14]=1)([CH3:6])[CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehydeHCID 684567162-[3-Methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-2-methyl-propionic acid ethyl ester

Product 1

HCID 684549242-{3-[1-(3,5-Diethoxy-4-pyrrol-1-yl-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 2-[3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-2-methyl-propionic acid ethyl ester [example 66b)] 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 yellow oil. MS: 608.4 (MH+).

Sources & evidence

ORD record
ord-2b0fb0e92ade46a1be5aaa070b0c567b
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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