Diisopropylethylamine → N-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-2-trifluoromethoxy-benzamide

HRID 2235466Notes

Reaction equation

HRID 2235466 reaction equation
[NH2:1][C:2]1[NH:21][C:5]2=[CH:6][C:7]3[C:8]([CH3:20])([CH3:19])[C:9](=[O:18])[N:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]=3[CH:12]=[C:4]2[N:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[F:53][C:54]([F:66])([F:65])[O:55][C:56]1[CH:64]=[CH:63][CH:62]=[CH:61][C:57]=1[C:58](O)=[O:59]>C1COCC1>[CH3:19][C:8]1([CH3:20])[C:7]2[CH:6]=[C:5]3[NH:21][C:2]([NH:1][C:58](=[O:59])[C:57]4[CH:61]=[CH:62][CH:63]=[CH:64][C:56]=4[O:55][C:54]([F:53])([F:65])[F:66])=[N:3][C:4]3=[CH:12][C:11]=2[N:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]1=[O:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27772232-(Trifluoromethoxy)benzoic acidHCID 593008242-Amino-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Product 1

HCID 59300870N-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-2-trifluoromethoxy-benzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of D5 (849 mg), TBTU (987 mg; 3.07 mmol) and DIPEA (1 ml) in THF (25 ml) is added drop-wise a solution of 2-trifluoromethoxy-benzoic acid (737 mg; 3.58 mmol) in THF (5 ml) at 0° C. over a period of 15 min. The reaction mixture is warmed to RT and stirred for 20 h. After completion of the reaction the solution is filtered over Alox B and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with cyclohexane/EtOAc yield the desired compound (736 mg).

Workup

  1. customAfter completion of the reaction the solution
  2. filtrationis filtered over Alox B
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel eluting with cyclohexane/EtOAc

Sources & evidence

ORD record
ord-310927259a32447fbb0c7b502f477e2e
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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