Acetonitrile → HCID 178493868, compound

HRID 536273Notes

Reaction equation

HRID 536273 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[N:17]([CH2:33][CH2:34][N:35]=3)[C:18]([NH:24][C:25]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:26])=[N:19][C:20]=2[C:21]=1[O:22][CH3:23])(C)(C)C.C(#N)C>FC(F)(F)C(O)=O.ClCCl>[NH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[N:17]([CH2:33][CH2:34][N:35]=3)[C:18]([NH:24][C:25](=[O:26])[C:27]3[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=3)=[N:19][C:20]=2[C:21]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 178493869HCID 178493869, compound

Product 1

HCID 178493868HCID 178493868, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl[3-({7-methoxy-5-[(pyridin-3-ylcarbonyl)amino]-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl}oxy)propyl]carbamate (Step 1, 1.2 g, 2.3 mmol) was diluted in a mixture of trifluoroacetic acid (6 mL) and dichloromethane (24 mL). The mixture was stirred at rt overnight, then was concentrated in vacuo to afford a viscous yellow oil. Acetonitrile was added to the mixture, and the desired was isolated by vacuum filtration as a white solid (0.55 g, 60%). 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.13 (2H, m), 3.02 (2H, m), 4.01 (3H, s), 4.25 (2H, m), 4.35 (2H, t), 4.57 (2H, m), 7.45 (1H, d), 7.73 (1H, m), 7.92 (2H, br m), 8.06 (1H, d), 8.69 (1H, m), 8.87 (1H, m), 9.43 (1H, m).

Workup

  1. concentrationwas concentrated in vacuo
  2. customto afford a viscous yellow oil

Sources & evidence

ORD record
ord-790fa02070bb4b88b30510bbfc2e9c93
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

Loading…