HCID 57794658, compound → HCID 57794665, compound

HRID 2099804Notes

Reaction equation

HRID 2099804 reaction equation
C(OC(=O)[NH:7][CH:8]([C:20]1[N:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]2=[N:22][N:21]=1)[CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH3:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[N:22]1[N:21]=[C:20]([CH:8]([NH2:7])[CH2:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([CH3:19])[CH:18]=2)[NH:15][N:14]=[CH:13]3)[N:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=12

Participants

3

Reactant 1

HCID 57794658HCID 57794658, compound

Product 1

HCID 57794665HCID 57794665, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl-1-([1,2,4]triazolo[4,3-a]pyridine-3-yl)-2-(7-methyl-1H-indazol-5-yl)ethylcarbamate (43.2 mg, 0.11 mmol) was dissolved in a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) and stirred under nitrogen for 1 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cationic exchange column. After washing the column with several volumes of methanol, the desired amine was obtained by washing the column with 2M ammonia in methanol. Concentration afforded 33 mg (93%) of the crude product which was used without purification. 1H-NMR (CD3OD, 300 MHz) δ 2.41 (s, 3H), 3.50-3.66 (m, 2H), 5.50 (bs, 2H), 6.63 (dd, J=6.6, 6.2, 1H), 6.95 (s, 1H), 7.11-7.20 (s, 1H), 7.38 (s, 1H), 7.71 (d, J=9.2, 1H), 7.88 (d, J=7.0, 1H), 7.91 (s, 1H). Mass spec.: 293.02 (MH)+.

Workup

  1. customThe solvent was removed in vacuo
  2. washAfter washing the column with several volumes of methanol

Sources & evidence

ORD record
ord-4551ebbf77bd43fd97b82483e7d71d56
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

Loading…