Trifluoroacetic acid → HCID 178432071, compound

HRID 1469105Notes

Reaction equation

HRID 1469105 reaction equation
[N:1]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]5[N:29]=[C:28]([CH3:30])[N:27](COCC[Si](C)(C)C)[C:24]5=[N:25][CH:26]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[N:1]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]5[N:29]=[C:28]([CH3:30])[NH:27][C:24]5=[N:25][CH:26]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67513853HCID 67513853, compound

Product 1

HCID 178432071HCID 178432071, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.19 g of 4-(3,4-dihydro-2H-quinolin-1-yl)-6-[2-methyl-3-(2-trimethylsilanylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]quinazoline and 200 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 48 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 14 min.), giving 0.03 g of 4-(3,4-dihydro-2H-quinolin-1-yl)-6-(2-methyl-3H-imidazo-[4,5-b]pyridin-6-yl)quinazoline (“A5”) as white solid (yield 23%, content 99%); MS-FAB (M+H+)=393.1; Rf (polar method): 1.41 min;

Workup

  1. custom(HPLC check, about 48 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 14 min.)

Sources & evidence

ORD record
ord-4817ac37c75e42d09482bbc9f8a3cec0
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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