Diisopropylethylamine → HCID 68455597, compound

HRID 502455Notes

Reaction equation

HRID 502455 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1)[C:8]([NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH3:26])[C:21](F)=[C:20]([O:28][CH2:29][CH3:30])[CH:19]=2)[CH2:13][CH2:12]1)=[O:9])#[N:2].C(OC(=O)C1C=C(OCC)C([Cl:49])=C(OCC)C=1)C.ClC1C(OCC)=CC(CN2CCC(NC(=O)C3C=C(OC)C=C(CO)C=3)CC2)=CC=1OCC.C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[Cl:49][C:21]1[C:22]([O:24][CH2:25][CH3:26])=[CH:23][C:18]([CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([NH:10][C:8](=[O:9])[C:7]3[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:5]([O:4][CH2:3][C:1]#[N:2])[CH:6]=3)[CH2:12][CH2:13]2)=[CH:19][C:20]=1[O:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 68456709N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamide 4-Chloro-3,5-diethoxy-benzoic acid ethyl esterHCID 684569833-Cyanomethoxy-N-[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-benzamide

Product 1

HCID 68455597HCID 68455597, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 3-cyanomethoxy-5-methoxy-N-piperidin-4-yl-benzamide (example 245) was reacted with 4-chloro-3,5-diethoxy-benzaldehyde (example 219), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as off-white solid. MS: 502.2 (MH+).

Sources & evidence

ORD record
ord-e6e48fb769d64284b5ac7fd69dfa89cc
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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