Triethylamine → HCID 178490478, compound

HRID 923568Notes

Reaction equation

HRID 923568 reaction equation
[C:1]([C:3]1[CH:42]=[CH:41][C:6]([CH2:7][N:8]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:9](=[O:32])[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[C:27]([F:30])([F:29])[F:28])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.Cl.[NH2:51][OH:52]>CN(C=O)C.O>[OH:52][NH:51][C:1]([C:3]1[CH:42]=[CH:41][C:6]([CH2:7][N:8]([CH2:33][C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C:9](=[O:32])[C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:31])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[C:27]([F:29])([F:28])[F:30])=[CH:14][CH:15]=2)=[CH:5][CH:4]=1)=[NH:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 71076634tert-butyl 2-(N-(4-cyanobenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate

Product 1

HCID 178490478HCID 178490478, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Prepared using General Procedure 19: To a stirring solution of tert-butyl 2-(N-(4-cyanobenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate INT-32 (229 mg, 0.394 mmol) in DMF (3 mL) were added triethylamine (142 μl, 0.984 mmol) and hydroxylamine hydrochloride (68.4 mg, 0.984 mmol). After stirring at room temperature for 72 h, the reaction mixture was diluted with water (50 mL) and extracted with DCM (3×20 mL). The organics were dried over MgSO4 and evaporated. The crude product was purified by column chromatography (MeOH/DCM) to yield 107 mg (44%) of tert-butyl 2-(N-(4-(N-hydroxycarbamimidoyl)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate INT-33. LCMS-ESI (m/z) calculated for C31H33F3N4O6: 614; found 615 [M+H]+, tR=1.70 min (Method 10).

Workup

  1. customPrepared
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialThe organics were dried over MgSO4
  4. customevaporated
  5. customThe crude product was purified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-2a0ac798b75043368fb9b4e12120f72c
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

Loading…