Trifluoroacetic acid → N-[2-[6-[1,6-dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]ethyl]-acetamide

HRID 2387712Notes

Reaction equation

HRID 2387712 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[N:14]=[C:13]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[N:19]=3)=[CH:17][C:12]2=[C:11]2[N:30]([CH3:33])[CH:31]=[N:32][C:10]=12)C)(C)(C)C.FC(F)(F)C(O)=O.CN1C(=O)CCC1>C(Cl)Cl>[CH3:33][N:30]1[C:11]2=[C:12]3[CH:17]=[C:16]([C:18]4[N:19]=[C:20]([CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH:21]=[CH:22][CH:23]=4)[NH:15][C:13]3=[N:14][C:9]([NH:7][CH3:6])=[C:10]2[N:32]=[CH:31]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13387N-methyl-2-pyrrolidoneHCID 131728185HCID 131728185, compound

Product 1

HCID 60133736N-[2-[6-[1,6-dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A450.4 (147 mg, 0.30 mmol), was dissolved in DMA (5 mL) and the solution heated to 77° C. One equivalent of 1.0M potassium t-butoxide in THF (0.3 ml, 0.30 mmol) was quickly added and the reaction heated at 70° C. for thirty minutes. A second equivalent of 1.0M potassium t-butoxide in THF (0.3 ml, 0.30 mmol) was quickly added and the reaction mixture stirred an additional thirty minutes. The reaction mixture was concentrated in vacuo. The crude product residue was purified by Silica Gel (230-400 Mesh) chromatography eluting with 2-5% MeOH/CH2Cl2 to give the Boc-protected intermediate, tert-butyl-7-(6-(2-acetamidoethyl)pyridin-2-yl)-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-4-yl(methyl)carbamate as an off-white solid. (76 mg, 52% yield). The solid was dissolved in methylene chloride (0.5 mL) and trifluoroacetic acid (0.5 mL) was added and the reaction mixture stirred for 0.25 h. The solvent was evaporated under reduced pressure to provide A450 (37 mg, 63%). M+H+=364.26. 1H NMP (400 MHz) MEOD δ 8.14 (s, 1H), 7.84 (m, 2H), 7.52 (s, 1H), 7.30 (m, 1H), 4.18 (s, 3H), 3.77 (m, 2H), 3.29 (s, 3H), 3.11 (m, 2H), 1.94 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto provide A450 (37 mg, 63%)

Sources & evidence

ORD record
ord-c3500a2dfc324ffc9c145d63beff27db
Source dataset
uspto-grants-2012_09
Patent number
US08268855B2

Reaction notes

Loading…