Trifluoroacetic acid → HCID 178433917, compound

HRID 1398561Notes

Reaction equation

HRID 1398561 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]([C:22]4[N:23]=[CH:24][N:25](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:26]=4)([OH:21])[CH3:20])[CH:15]=3)[C:10]([CH3:46])=[N:9]2)[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]([C:22]4[N:23]=[CH:24][NH:25][CH:26]=4)([OH:21])[CH3:20])[CH:15]=3)[C:10]([CH3:46])=[N:9]2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 681818514-[1-(2-Aminopyrimidin-4-yl)-3-methylindazol-6-yl]-2-[1-(triphenylmethyl)imidazol-4-yl]but-3-yn-2-ol

Product 1

HCID 178433917HCID 178433917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[1-(2-aminopyrimidin-4-yl)-3-methylindazol-6-yl]-2-[1-(triphenylmethyl)imidazol-4-yl]but-3-yn-2-ol (45 mg, 0.07 mmol) in DCM (2 ml) was added trifluoroacetic acid (0.4 ml). The reaction was allowed to stand at RT for 0.5 hr and then concentrated in vacuo. DCM (5 mL) and saturated aqueous sodium bicarbonate (2 mL) were added and the organics extracted (4×5 mL DCM extractions). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Isolute, 0-10% methanol gradient in DCM) to surrender the title compound as a pale brown solid: 1H NMR (250 MHz, MeOD) delta 1.92 (3H, s), 2.58 (3H, s), 7.28-7.14 (2H, m), 7.39 (1H, dd, J=8.2, 1.2 Hz), 7.82-7.64 (2H, m), 8.19 (1H, d, J=5.8 Hz), 8.98 (1H, s); LC-MS: m/z=+360.05 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionDCM (5 mL) and saturated aqueous sodium bicarbonate (2 mL) were added
  3. extractionthe organics extracted
  4. extraction(4×5 mL DCM extractions)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (Isolute, 0-10% methanol gradient in DCM)

Sources & evidence

ORD record
ord-8a11538a881b47268309f61abd186bb2
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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