5-Hexynenitrile → N-[3-(5-Cyano-pent-1-ynyl)-benzyloxy]-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 1663132Notes

Reaction equation

HRID 1663132 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][NH:7][C:8](=[O:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[C:27]([CH2:29][CH2:30][CH2:31][C:32]#[CH:33])#[N:28]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:27]([CH2:29][CH2:30][CH2:31][C:32]#[C:33][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][NH:7][C:8](=[O:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)#[N:28]

Participants

4

Reactant 2

HCID 1398525-HexynenitrileHCID 58989772N-(3-Iodo-benzyloxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

Product 1

HCID 11362277N-[3-(5-Cyano-pent-1-ynyl)-benzyloxy]-2-[(pyridin-4-ylmethyl)-amino]-benzamide

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The same procedure was used as described for the preparation of example 365, but without addition of tetrabutylammonium iodide. Starting materials: N-(3-Iodo-benzyloxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide (see example 361) and 5-cyano-1-pentyne (Aldrich).

Workup

  1. customas described for the preparation of example 365

Sources & evidence

ORD record
ord-36bd0d95c4e84b2c800cf7e17d8ea317
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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