HCID 178493840, compound → HCID 178493838, compound

HRID 1259508Notes

Reaction equation

HRID 1259508 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[O:15])[N:9]3[CH2:22][CH2:23][N:24]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:25][CH2:26][CH2:27][CH:28]1[O:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]1>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:14](=[O:15])[C:16]3[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=3)[N:9]3[CH2:22][CH2:23][N:24]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:25][CH2:26][CH2:27][CH:28]1[O:33][CH2:32][CH2:31][NH:30][CH2:29]1

Participants

3

Reactant 1

HCID 178493840HCID 178493840, compound

Product 1

HCID 178493838HCID 178493838, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 2-[2-({7-methoxy-5-[(pyridin-3-ylcarbonyl)amino]-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl}oxy)ethyl]morpholine-4-carboxylate (650 mg, 1.44 mmol) was dissolved in trifluoroacetic acid (10 mL) and stirred at rt for 4 h. The reaction mixture was concentrated under reduced pressure, and the resulting oil was diluted with methanol (1 mL) and pulled through a silica bound-NH2 cartridge. The solution was concentrated under reduced pressure to give the title compound as a solid (45 mg, 69%): HPLC MS RT=0.21 min, MH+=451.1; 1H NMR (DMSO-d6) δ: 12.8-12.7 (1H, br s), 9.32 (1H, s), 8.73 (1H, d), 8.46 (1H, d), 7.60 (1H, d), 7.54-7.49 (1H, m), 7.06 (1H, d) 4.22-3.99 (6H, m), 3.94 (3H, s), 3.78 (1H, d), 3.66-3.58 (1H, m), 3.47 (1H, t), 2.95 (1H, d), 2.82-2.65 (2H, m), 1.98-1.78 (2H, m).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe resulting oil was diluted with methanol (1 mL)
  3. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae4731b5debf4ee5b9b046f695be2459
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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