HCID 178493909, compound → HCID 178493908, compound

HRID 536268Notes

Reaction equation

HRID 536268 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][O:28][CH2:29][CH2:30][NH:31]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:9]([CH2:22][CH2:23][N:24]=3)[C:10]([NH:13][C:14](=[O:15])[C:16]3[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=3)=[N:11][C:12]=2[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 178493909HCID 178493909, compound

Product 1

HCID 178493908HCID 178493908, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl {2-[2-({7-methoxy-5-[(pyridin-3-ylcarbonyl)amino]-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl}oxy)ethoxy]ethyl}carbamate (Step 3, 3.6 g, 6.8 mmol) was diluted in a mixture of trifluoroacetic acid (18 mL) and dichloromethane (70 mL). The mixture was stirred at rt overnight, then was concentrated in vacuo. The resultant orange oil was redissolved in dichloromethane and treated with an excess of triethylamine. After stirring at rt for 0.5 h, the solvent was evaporated under reduced pressure and the residue triturated with ethyl acetate. The title compound was isolated by vacuum filtration and dried in the vacuum oven. This material was contaminated with a small amount of triethylamine, but was suitable for use in the next step as is. HPLC MS RT=1.09 min, MH+=425.2. 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.01 (2H, m), 3.69 (2H, t), 3.89 (2H, m), 4.02 (3H, s), 4.26 (2H, m), 4.44 (2H, m), 4.57 (2H, m), 7.49 (1H, d), 7.76 (1H, m), 8.05 (1H, d), 8.72 (1H, m), 8.89 (1H, m), 9.44 (1H, m).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe resultant orange oil was redissolved in dichloromethane
  3. additiontreated with an excess of triethylamine
  4. stirringAfter stirring at rt for 0.5 h
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-781c7e9b149e4081ac3670f09073a6fe
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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