Trifluoroacetic acid → HCID 178432070, compound

HRID 1469102Notes

Reaction equation

HRID 1469102 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]3[CH:22]=[C:23]4[N:29]=[C:28]([CH3:30])[N:27](COCC[Si](C)(C)C)[C:24]4=[N:25][CH:26]=3)[CH:19]=2)[N:14]=[CH:13][N:12]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]3[CH:22]=[C:23]4[N:29]=[C:28]([CH3:30])[NH:27][C:24]4=[N:25][CH:26]=3)[CH:19]=2)[N:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67517091HCID 67517091, compound

Product 1

HCID 178432070HCID 178432070, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.70 g of 4-(3,4-dihydro-1H-isoquinolin-2-yl)-6-[2-methyl-3-(2-trimethylsilanylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]quinazoline and 825 μl of trifluoroacetic acid in 8 ml of dichloromethane are stirred at 25° C. in a flask until the reaction is complete (HPLC check, about 120 hours). The cooled reaction solution is diluted with dichloromethane and washed with sodium hydrogencarbonate solution. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient EA: methanol 0-30% in 13 min), giving 0.19 g of 4-(3,4-dihydro-1H-isoquinolin-2-yl)-6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)quinazoline (“A4”) as white solid (yield 36%, content 97%); MS-FAB (M+H+)=393.1; Rf (polar method): 1.39 min;

Workup

  1. custom(HPLC check, about 120 hours)
  2. customThe cooled reaction solution
  3. washwashed with sodium hydrogencarbonate solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. custompurified by means of column chromatography (gradient EA: methanol 0-30% in 13 min)

Sources & evidence

ORD record
ord-77a1c191fa6e493fa0a47c9981841bc3
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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