1-Hydroxybenzotriazole → HCID 67007536, compound

HRID 564021Notes

Reaction equation

HRID 564021 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:11]([O:15][C:16](=[O:27])[C:17]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:19]([C:20](O)=[O:21])[CH:18]=1)([CH3:14])([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[C:11]([O:15][C:16](=[O:27])[C:17]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:19]([C:20]([NH:10][C:8]2[CH:9]=[C:4]3[CH:3]=[CH:2][NH:1][C:5]3=[N:6][CH:7]=2)=[O:21])[CH:18]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineHCID 67007591HCID 67007591, compound

Product 1

HCID 67007536HCID 67007536, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridin-5-ylamine (example c), 0.5 mmol) and 4-methyl-isophthalic acid 1-tert-butyl ester from example 1-1 (0.5 mmol) in THF (5 ml) were added TBTU (0.5 mmol), HOBT (0.5 mmol) and Hunig's base (0.6 mmol) and stirred at RT for overnight. Solvent was concentrated, residue was diluted with EtOAc ( ), washed with 1(N) NaOH. Organics was concentrated to get 2.8 g of the crude title product. LC-MS: (m/z 352)

Workup

  1. concentrationSolvent was concentrated
  2. additionresidue was diluted with EtOAc ( ),
  3. washwashed with 1(N) NaOH
  4. concentrationOrganics was concentrated

Sources & evidence

ORD record
ord-f869ecd7ee18453aa6f1719f9d15cdd0
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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