Diisopropylethylamine → Ethyl 2-(((2-(4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)cyclopentyl)methyl)amino)-2-oxoacetate

HRID 1407050Notes

Reaction equation

HRID 1407050 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([NH:20][C:21]3[N:26]=[C:25]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:24]=[C:23]([NH:33][C:34]4[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=4)[N:22]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[NH2:43][CH:44]1[CH2:48][CH2:47][CH2:46][CH:45]1[CH2:49][NH:50][C:51](=[O:57])[C:52]([O:54][CH2:55][CH3:56])=[O:53].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([NH:20][C:21]3[N:26]=[C:25]([O:27][CH2:28][C:29]([F:30])([F:32])[F:31])[N:24]=[C:23]([NH:33][C:34]4[CH:35]=[CH:36][C:37]([C:38]([NH:43][CH:44]5[CH2:48][CH2:47][CH2:46][CH:45]5[CH2:49][NH:50][C:51](=[O:57])[C:52]([O:54][CH2:55][CH3:56])=[O:53])=[O:39])=[CH:41][CH:42]=4)[N:22]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667654164-(4-(1-(4-Chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acidHCID 86691689Ethyl 2-(((2-aminocyclopentyl)methyl)amino)-2-oxoacetate

Product 1

HCID 86691688Ethyl 2-(((2-(4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)cyclopentyl)methyl)amino)-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

iPr2NEt (0.5 mL) was added into a solution of 4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoic acid (300 mg), ethyl 2-(((2-aminocyclopentyl)methyl)amino)-2-oxoacetate (205 mg) and TBTU (201 mg) in THF (10 mL). The reaction was stirred at room temperature for 16 hours before being quenched by water. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic phase was dried over MgSO4 and concentrated under vacuum to give the crude ethyl 2-(((2-(4-((4-((1-(4-chlorophenyl)cyclopropyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)cyclopentyl)methyl)amino)-2-oxoacetate which was used as was.

Workup

  1. custombefore being quenched by water
  2. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-974e60842289412ba24cf85fbccdcc6e
Source dataset
uspto-grants-2014_12
Patent number
US08916702B2

Reaction notes

Loading…