HCID 136065309, compound → HCID 136065306, compound

HRID 490155Notes

Reaction equation

HRID 490155 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[C:3]([O:5][CH2:6][C:7]1[NH:16][C:15](=[O:17])[C:14]2[C:9](=[CH:10][C:11]3[CH2:20][CH2:19][CH:18]([N:21]([C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31]C(C)(C)C)=[O:30])=[CH:27][CH:26]=4)[CH2:22][C:23]#[CH:24])[C:12]=3[CH:13]=2)[N:8]=1)=[O:4]>FC(F)(F)C(O)=O>[CH3:1][C:2]([CH3:39])([CH3:38])[C:3]([O:5][CH2:6][C:7]1[NH:16][C:15](=[O:17])[C:14]2[C:9](=[CH:10][C:11]3[CH2:20][CH2:19][CH:18]([N:21]([C:25]4[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:36][CH:37]=4)[CH2:22][C:23]#[CH:24])[C:12]=3[CH:13]=2)[N:8]=1)=[O:4]

Participants

3

Reactant 1

HCID 136065309HCID 136065309, compound

Product 1

HCID 136065306HCID 136065306, compoundYield 114%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-[N-((6RS)-2-(2,2dimethylpropionyloxymethyl)-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop2-ynyl)amino]-benzoate (80 mg, 0.15 mmol) in trifluoroacetic acid (5 ml) was stirred at room temperature with protection from the light for 1.5 h. The solvent was removed in vacuo and the residue triturated with 1:1 diethyl ether and hexane to yield the desired product as a white solid (81 mg, TFA salt); m.p. 133° C., 1H-NMR (DMSO-d6) δ 1.23 (s, 9H, CO2CMc3), 2.22 (m, 1H, 7-H), 2.50 (m, 1H, 7-H), 3.03 (m, 2H, 8-H), 3.14 (s, 1H, propargyl CH), 3.97 (AB system, J=18.8 Hz, 2H, propargyl CH2), 4.95 (s, 2H, 2-CH2), 5.79 (t, J=8.6 Hz, 1H, 6-H), 7.03 (d, J=9.0 Hz, 2H, 3′-H, 5′-H), 7.51 (s, 1H, 9-H), 7.81 (d, J=6.6 Hz, 2H, 2′-H, 6′-H), 7.83 (s, 1H, 5-H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue triturated with 1:1 diethyl ether and hexane

Sources & evidence

ORD record
ord-b04288e4a8e44104a31eb06075ab10f9
Source dataset
uspto-grants-2009_05
Patent number
US07528141B2

Reaction notes

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