HCID 58081300, compound → HCID 58081242, compound

HRID 928453Notes

Reaction equation

HRID 928453 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([NH:19][CH2:20][C:21]4[C:22]([CH3:36])=[CH:23][C:24]([NH:28]C(=O)OC(C)(C)C)=[N:25][C:26]=4[CH3:27])=[O:18])[CH:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:37]>C(Cl)Cl>[NH2:28][C:24]1[N:25]=[C:26]([CH3:27])[C:21]([CH2:20][NH:19][C:17]([C:15]2[CH:14]=[N:13][N:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:2]([CH3:1])[C:3]([CH3:37])=[CH:4]4)[CH:16]=2)=[O:18])=[C:22]([CH3:36])[CH:23]=1

Participants

3

Reactant 1

HCID 58081300HCID 58081300, compound

Product 1

HCID 58081242HCID 58081242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl 5-((1-((1,2-dimethyl-1H-indol-5-yl)methyl)-1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate (160 mg, 0.318 mmol) in DCM (5 ml) Silica gel (2000 mg) was added. The resulting suspension was concentrated under vacuum to dryness and kept at 75° C. for 6 days under high vacuum. The mixture was taken up in suspended in DCM/NH3 (in MeOH 7N) 9:1, the solution was filtered of and concentrated under reduced pressure to afford the title compound. The crude product was purified by preparative HPLC (Waters Sunfire Prep C18 ODB 5 um, 30×100 mm, 1 to 99% ACN and 0.1% TFA, flow 45 ml/min) to yield pure title compound.

Workup

  1. concentrationThe resulting suspension was concentrated under vacuum to dryness
  2. filtrationthe solution was filtered of and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4874f186589e4900af974a1b22f09f69
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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