Diisopropylethylamine → HCID 68563383, compound

HRID 2108501Notes

Reaction equation

HRID 2108501 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH:21]4[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]4)=[CH:17][NH:18]3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[F:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([F:37])[CH:36]=1)[C:31](O)=[O:32].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([F:37])[CH:36]=1)[C:31]([N:23]1[CH2:24][CH2:25][CH2:26][CH:21]([C:16]2[C:15]3[C:19](=[CH:20][C:12]([C:10]([N:7]4[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]4)=[O:11])=[CH:13][CH:14]=3)[NH:18][CH:17]=2)[CH2:22]1)=[O:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1012653,5-Difluorobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68565693HCID 68565693, compound

Product 1

HCID 68563383HCID 68563383, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.02 g (0.56 mmol) (4-isopropyl-piperazin-1-yl)-(3-piperidin-3-yl-1H-indol-6-yl)-methanone, 0.01 g (0.06 mmol) 3,5-difluorobenzoic acid, 0.02 g (0.06 mmol) TBTU and 0.044 g (0.3 mmol) DIPEA in 0.8 mL DMF was stirred at room temperature for 16 h. The mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. Evaporation of the product fractions yielded 16 mg (57%) of the title compounds as off-white foam. MS (m/e): 495.4 (MH+).

Workup

  1. customThe mixture was subjected to preparative HPLC purification on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile/water/NEt3
  4. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-d72e5831fe1445aa8d889fefa5fa6c63
Source dataset
uspto-grants-2009_04
Patent number
US07514433B2

Reaction notes

Loading…