O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 24948453, compound

HRID 467585Notes

Reaction equation

HRID 467585 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([N:12]1[CH2:19][C:18]2[C:14](=[N:15][NH:16][C:17]=2[NH:20][C:21](=[O:31])[C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=2)[C:13]1([CH3:33])[CH3:32])=[O:11].[CH3:34][N:35]1[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([N:12]1[CH2:19][C:18]2[C:17]([NH:20][C:21](=[O:31])[C:22]3[CH:23]=[CH:24][C:25]([C:26]([NH:41][CH:38]4[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]4)=[O:28])=[CH:29][CH:30]=3)=[N:16][NH:15][C:14]=2[C:13]1([CH3:32])[CH3:33])=[O:11]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidineHCID 178422373HCID 178422373, compound

Product 1

HCID 24948453HCID 24948453, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[5-(2,6-Dichloro-phenylcarbamoyl)-6,6-dimethyl-2,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazol-3-yl]-terephthalamic acid (0.11 g, 0.22 mmol) N,N-diispropylethylamine (0.12 mL, 0.66 mmol) 1-Methyl-piperidin-4-ylamine (0.04 g, 0.34 mmol) in dry CH2Cl2 (20 mL), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.11 g, 0.34 mmol) was added. The reaction was stirred at room temperature over night, the solvent removed under reduced pressure, the residue dissolved in CH2Cl2 (40 mL) and washed with water (1×20 mL) then with saturated sodium hydrogencarbonate aqueous solution (1×20 mL). The organic phase was dried over sodium sulphate, the solvent evaporated in vacuo and the crude product purified by flash chromatography (CH2Cl2/MeOH/NH3 90/10/1) to afford 0.07 g (yield 55%) of the title compound.

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionthe residue dissolved in CH2Cl2 (40 mL)
  3. washwashed with water (1×20 mL)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customthe solvent evaporated in vacuo
  6. customthe crude product purified by flash chromatography (CH2Cl2/MeOH/NH3 90/10/1)

Sources & evidence

ORD record
ord-8eba57b6f77c40eaa615349b5811625c
Source dataset
uspto-grants-2014_01
Patent number
US08623876B2

Reaction notes

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