Diisopropylethylamine → HCID 11328076, compound

HRID 2225307Notes

Reaction equation

HRID 2225307 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([N:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[CH2:4][C@H:3]1[CH2:13][C:14]#[N:15].C(N(C(C)C)CC)(C)C.[F:25][C:26]([F:41])([F:40])[C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=1)[C:30]([NH:32][CH2:33][C:34](O)=[O:35])=[O:31].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(#N)C.CO>[C:14]([CH2:13][C@@H:3]1[CH2:4][C@H:5]([N:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[CH2:6][CH2:7][C@@H:2]1[NH:1][C:34](=[O:35])[CH2:33][NH:32][C:30](=[O:31])[C:29]1[CH:37]=[CH:38][CH:39]=[C:27]([C:26]([F:25])([F:41])[F:40])[CH:28]=1)#[N:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 69285582HCID 69285582, compound

Product 1

HCID 11328076HCID 11328076, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-((1S,2S,5R)-2-amino-5-(isopropyl(methyl)amino)cyclohexyl)acetonitrile (100 mg, 0.27 mmoles) in 2 ml of anhydrous acetonitrile were added diisopropylethylamine (0.24 ml, 1.35 mmoles), 2-(3-(trifluoromethyl)benzamido)acetic acid (66.6 mg, 0.27 mmoles) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (95.2 mg, 0.3 mmoles, Bachem), and the mixture was stirred for 18 hours at room temperature. Then several drops of methanol was added, and it was stirred for additional two hours. The solvent was evaporated off and the residue was purified by chromatography (silica gel, 0.7:6.3:93 cNH4H-MeOH—CH2Cl2) to give N-(2-((1S,2S,4R)-2-(cyanomethyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide. MS found: (M+H)+=439.3.

Workup

  1. stirringit was stirred for additional two hours
  2. customThe solvent was evaporated off
  3. customthe residue was purified by chromatography (silica gel, 0.7:6.3:93 cNH4H-MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-f1622ab6ad0d4002b9306e4017c6c258
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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