HCID 136065296, compound → HCID 136065301, compound

HRID 1297516Notes

Reaction equation

HRID 1297516 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][C:8]3[CH2:17][CH2:16][CH:15]([N:18]([C:22]4[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[CH:24][CH:23]=4)[CH2:19][C:20]#[CH:21])[C:9]=3[CH:10]=2)[N:5]=1>ClCCl.FC(F)(F)C(O)=O>[CH3:1][O:2][CH2:3][C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][C:8]3[CH2:17][CH2:16][CH:15]([N:18]([C:22]4[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:33][CH:34]=4)[CH2:19][C:20]#[CH:21])[C:9]=3[CH:10]=2)[N:5]=1

Participants

4

Reactant 1

HCID 136065296HCID 136065296, compound

Product 1

HCID 136065301HCID 136065301, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-{N-[(6RS)-2-methoxymethyl-4-oxo-3,4,7,8-tetra-hydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoate (0.069 g, 0.15 mmol) in dichloromethane (1 ml) and trifluoroacetic acid (3 ml) was stirred at room temperature for 1 hour and 10 min, then the solvents were removed in vacuo. The residue was triturated with diethyl ether and the precipitate was collected by filtration, washed with diethyl ether and dried in vacuo over P2O5 to afford the title compound as the tifluoroacetate salt: 0.061 g, m.p. 225° C. (dec); 1H-NMR (250 MHz, DMSO-d6, TMS) 2.23, 2.53 (obscured by DMSO peak) (2×m, each 1H, 7-H), 2.90-3.20 (m, 3H, C≡CH, 8-H), 3.34 (s (obscured by the H2O peak), 3H, OCH3), 3.97 (ABq, J=18.0 Hz, 2H, CH2C≡C), 4.32 (s, 2H, 2-CH2), 5.79 (t, J=8.1 Hz, 1H, 6-H), 7.03 (d, J=9.02 Hz, 2H, 3′, 5′-H), 7.58, (s, 1H, 9-H), 7.81 (m, 3H, 5-H, 2′, 6′-H), 12.17 (s, 1H, N3-H); MS (ESI, m/z) 426 {(M+Na)+, 25%}, 404 {(M+H)+, 70%}.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was triturated with diethyl ether
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with diethyl ether
  5. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-bede690f4cad46a3b271ae8457fcf254
Source dataset
uspto-grants-2007_07
Patent number
US07250511B2

Reaction notes

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