Trifluoroacetic acid → HCID 178432072, compound

HRID 1469111Notes

Reaction equation

HRID 1469111 reaction equation
[CH3:1][C:2]1[N:31](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][N:14]=[C:13]4[N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23](=[O:30])[CH2:22][CH2:21]3)[CH:9]=[C:4]2[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[NH:31][C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][N:14]=[C:13]4[N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23](=[O:30])[CH2:22][CH2:21]3)[CH:9]=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67513135HCID 67513135, compound

Product 1

HCID 178432072HCID 178432072, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.25 g of 1-{6-[2-methyl-3-(2-trimethylsilanylethoxymethyl)-3H-imidazo[4,5-b]-pyridin-6-yl]quinazolin-4-yl}-2,3-dihydro-1H-quinolin-4-one and 255 μl of trifluoroacetic acid in 2 ml of dichloromethane are stirred at 25° C. in a flask until the reaction is complete (HPLC check, about 72 hours). The cooled reaction solution is evaporated to dryness in a rotary evaporator. The residue is purified by means of preparative HPLC (gradient water:acetonitrile 1-50% in 16 min.), giving 0.04 g of 1-[6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-quinazolin-4-yl]-2,3-dihydro-1H-quinolin-4-one (“A13”) as white solid (yield 23%, content 99%); MS-FAB (M+H+)=407.1; Rf (polar method): 1.50 min;

Workup

  1. custom(HPLC check, about 72 hours)
  2. customThe cooled reaction solution
  3. customis evaporated to dryness in a rotary evaporator
  4. customThe residue is purified by means of preparative HPLC (gradient water:acetonitrile 1-50% in 16 min.)

Sources & evidence

ORD record
ord-139a413badfa435bbe1feb56c615913d
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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