Triethylamine → 4-(Benzyloxy)-N-[5-cyano-2-(cyclohexylamino)phenyl]benzamide

HRID 392962Notes

Reaction equation

HRID 392962 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:22]#[N:23].C(N(CC)CC)C>ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:18][C:19]2[CH:20]=[C:21]([C:22]#[N:23])[CH:24]=[CH:25][C:26]=2[NH:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 738804-(Benzyloxy)benzoic acidHCID 226608193-Amino-4-(cyclohexylamino)benzonitrile

Product 1

HCID 226608044-(Benzyloxy)-N-[5-cyano-2-(cyclohexylamino)phenyl]benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the acid chloride of 4-benzyloxybenzoic acid (2.56 g, 10.4 mmol) in dichloromethane (30 mL) and dimethylformamide (5 mL) was added dropwise to a solution of compound 4 (2.23 g, 10.4 mmol) and triethylamine (2.4 mL, 17.2 mmol) in dichloromethane (15 mL). After 1.5 h, 4-dimethylaminopyridine (0.12 g) was added. The reaction was stirred at rt for 18 h and then heated to 45° C. for 4 h. The reaction was cooled to rt and then extracted with 1 N KHSO4 (1×) and brine (1×). The organic layer was dried (MgSO4) and concentrated on a rotary evaporator. The residue was purified by column chromatography (silica gel, 10-20% ethyl acetate/hexanes (v/v)) to afford compound 11 as a slightly purple solid (2.08 g, 47%). ESI-MS m/e 426.3 (M+1).

Workup

  1. temperatureheated to 45° C. for 4 h
  2. temperatureThe reaction was cooled to rt
  3. extractionextracted with 1 N KHSO4 (1×) and brine (1×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was purified by column chromatography (silica gel, 10-20% ethyl acetate/hexanes (v/v))

Sources & evidence

ORD record
ord-4c821ac4c3f240ea9d193d219652af36
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

Loading…