HCID 18416688, compound → HCID 135409270, compound

HRID 990798Notes

Reaction equation

HRID 990798 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[NH:21][N:20]=[C:19]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=2)=[CH:9]1)(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[NH:21][N:20]=[C:19]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=2)=[CH:9]1

Participants

3

Reactant 1

HCID 18416688HCID 18416688, compound

Product 1

HCID 135409270HCID 135409270, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[5-(N-BOC-indol-3-yl)-1H-pyrazol-3-yl]-phenyl-amine (332 mg, 0.89 mmol) was stirred in 50% TFA/CH2C12 (8 mL) at r.t. for 1 h, at which point material had precipitated to a solid block. Solvents were removed in vacuo, and the solid was dissolved in EtOAc (50 mL), washed with saturated NaHCO3 (25 mL) and brine (25 mL), dried (MgSO4) and concentrated in vacIto. Purification by silica gel chromatography (50% to 70% EtOAc/hexanes) gave 182 mg (75%) of [5-(1H-indol-3-yl)-1H-pyrazol-3-yl]-phenyl-amine as a white solid. 1H NMR (300 MHz, DMSO-d6) δ12.06 (s, 1H), 11.41 (s, 1H), 8.38 (s, 1H), 7.80 (d, 1H, J=6.3 Hz), 7.74 (d, 1H, J=2.7 Hz), 7.36-7.47 (m, 3H), 7.11-7.21 (m, 4H), 6.70 (t, 1H, J=7.2 Hz), 6.14 (s, 1H). Anal. (C17H14N4.0.05 H2O) C, H, N. Calculated C=74.19; H=5.16; N=20.36; found C=74.25; H=5.17; N=20.24.

Workup

  1. customat which point material had precipitated to a solid block
  2. customSolvents were removed in vacuo
  3. dissolutionthe solid was dissolved in EtOAc (50 mL)
  4. washwashed with saturated NaHCO3 (25 mL) and brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacIto
  7. customPurification by silica gel chromatography (50% to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e897ecda283b4ad695840eddbee43e03
Source dataset
uspto-grants-2002_10
Patent number
US06462069B2

Reaction notes

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