Diisopropylethylamine → HCID 69284606, compound

HRID 2225304Notes

Reaction equation

HRID 2225304 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][CH:14]([OH:18])[CH:15]([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C.[F:28][C:29]([F:44])([F:43])[C:30]1[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=1)[C:33]([NH:35][CH2:36][C:37]([OH:39])=[O:38])=[O:34].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(#N)C.CO>[OH:18][C@@H:14]([CH:15]([CH3:17])[CH3:16])[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:37](=[O:38])[CH2:36][NH:35][C:33](=[O:34])[C:32]1[CH:40]=[CH:41][CH:42]=[C:30]([C:29]([F:28])([F:44])[F:43])[CH:31]=1.[OH:18][C@H:14]([CH:15]([CH3:17])[CH3:16])[CH2:13][C@@H:3]1[CH2:4][C@H:5]([N:8]([CH:10]([CH3:11])[CH3:12])[CH3:9])[CH2:6][CH2:7][C@@H:2]1[NH:1][C:37](=[O:39])[CH2:36][NH:35][C:33](=[O:34])[C:32]1[CH:40]=[CH:41][CH:42]=[C:30]([C:29]([F:28])([F:44])[F:43])[CH:31]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 69285520HCID 69285520, compound

Product 2

HCID 69284606HCID 69284606, compoundHCID 69286024HCID 69286024, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6342AcetonitrileSolvent

Procedure

Examples 11p and 11q, Step 10: To a solution of 1-((1S,2S,5R)-2-amino-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-ol (0.38 mmoles) in 3 ml of anhydrous acetonitrile were added diisopropylethylamine (0.27 ml, 1.52 mmoles), 2-(3-(trifluoromethyl)benzamido)acetic acid (141 mg, 0.57 mmoles) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (183 mg, 0.57 mmoles, Bachem), and the mixture was stirred for 12.5 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, 1:9:90 cNH4OH-MeOH—CH2Cl2) to give N-(2-((1S,2S,4R)-2-((2R)-2-hydroxy-3-methylbutyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (Example 11p) and N-(2-((1S,2S,4R)-2-((2S)-2-hydroxy-3-methylbutyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (Example 11q). For both, MS found: (M+H)+=486.4.

Workup

  1. stirringit was stirred for additional two hours
  2. customThe solvent was evaporated off
  3. customthe residue was purified by chromatography (silica gel, 1:9:90 cNH4OH-MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-d13f208e844047118b500752bd20034d
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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