HCID 136334120, compound → HCID 135401926, compound

HRID 1297525Notes

Reaction equation

HRID 1297525 reaction equation
C([O:8][CH2:9][C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[CH:13][C:14]3[CH2:23][CH2:22][CH:21]([NH:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=4)[C:15]=3[CH:16]=2)[N:11]=1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH2:9][C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[CH:13][C:14]3[CH2:23][CH2:22][CH:21]([NH:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])=[CH:27][CH:26]=4)[C:15]=3[CH:16]=2)[N:11]=1

Participants

4

Reactant 1

HCID 136334120HCID 136334120, compound

Product 1

HCID 135401926HCID 135401926, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of tert-butyl 4-{N-[(6RS)-2-benzyloxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino}benzoate (1.40 g, 2.8 mmol) in EtOH (150 ml) was added 10% Pd/C (0.665 g). The mixture was stirred at 45° C. for 3 h, then more catalyst (0.200 g) was added and stirring was continued at 50° C. for 6 h. The catalyst was removed by filtration, washed with EtOH, and the filtrate was concentrated in vacuo. Purification of the residue by column chromatography, on elution with 8% methanol in ethyl acetate, gave a white solid (0.679 g, 60%); mp 265-266° C.; 1H-NMR (250 MHz, DMSO-d6, TMS) 1.52 (s, 9H, C(CH3)3), 1.88, 2.57 (2×m, 1H each, 7-CH), 2.90-3.17 (m, 2H, 8-CH2), 4.38 (d, J=6.0 Hz, 2H 2-CH2OH), 5.17 (m, 1H, 6-CH), 5.54 (t, J=6.1 Hz, 1H, CH2OH), 6.79 (d, J=8.8 Hz, 2H, 3′,5′-ArH), 6.91 (d, J=7.8 Hz, N10—H), 7.51, 7.91 (2×s, 1H each, 5-H and 9-H), 7.68 (d, J=8.8 Hz, 2H, 2′,6′-ArH), 11.83 (s, 1H, CONH); MS (ESI, m/z) 408 [M+H)+, 65%], 352 [(M-tBu)+, 100%], 215 (60%); Found: C, 67.41; H, 6.20; N, 10.17; C23H25N3O4 requires C, 67.80; H, 6.18; N, 10.31%.

Workup

  1. stirringstirring
  2. waitwas continued at 50° C. for 6 h
  3. customThe catalyst was removed by filtration
  4. washwashed with EtOH
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the residue by column chromatography
  7. washon elution with 8% methanol in ethyl acetate

Sources & evidence

ORD record
ord-b081c820f5e243e29c148380b8a0c1cd
Source dataset
uspto-grants-2007_07
Patent number
US07250511B2

Reaction notes

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