Trifluoroacetic acid → HCID 58574313, compound

HRID 1619362Notes

Reaction equation

HRID 1619362 reaction equation
C(OC([N:8]1[CH2:32][CH2:31][C:12]2=[N:13][C:14]3[CH:15]=[C:16]([C:22]#[C:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)[CH:17]=[CH:18][C:19]=3[C:20](=[O:21])[N:11]2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:30][C:26]1[CH:25]=[C:24]([C:23]#[C:22][C:16]2[CH:17]=[CH:18][C:19]3[C:20](=[O:21])[N:11]4[CH2:10][CH2:9][NH:8][CH2:32][CH2:31][C:12]4=[N:13][C:14]=3[CH:15]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58574259HCID 58574259, compound

Product 1

HCID 58574313HCID 58574313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl-8-(2-(3-fluorophenyl)ethynyl)-11-oxo-1,2,4,5-tetrahydro-[1,4]diazepino[7,1-b]quinazoline-3(11H)-carboxylate (1.3 g, 3.0 mmol) in DCM (30 mL) was added trifluoroacetic acid (15 mL). The mixture was stirred for 1 h at room temperature. Then the reaction mixture was concentrated and purified by silica gel chromatography to give the desired product. MS (ESI): 334 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.26-8.23 (d, J=8.2 Hz, 1H), 7.77 (s, 1H), 7.59-7.55 (d, J=8.3 Hz, 1.5 Hz, 1H), 7.38-7.34 (m, 2H), 7.29-7.26 (m, 1H), 7.14-7.09 (m, 1H), 4.53-4.50 (t, J=3.6 Hz, 2H), 3.24-3.17 (m, 4H), 3.11-3.10 (t, J=4.5 Hz, 2H). mGluR5 PAM EC50: ++.

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a3146aa7c5b542e9a8a02c50c6322eee
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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