HCID 71255363, compound → HCID 71254580, compound

HRID 540301Notes

Reaction equation

HRID 540301 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1([CH2:13][NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=3)[N:18]=[C:17]([N:26]3[CH2:32][CH2:31][C:30]([F:34])([F:33])[C:29]4[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=4[CH2:27]3)[N:16]=2)[CH2:12][O:11][CH2:10]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1([CH2:13][NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=3)[N:18]=[C:17]([N:26]3[CH2:32][CH2:31][C:30]([F:34])([F:33])[C:29]4[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=4[CH2:27]3)[N:16]=2)[CH2:10][O:11][CH2:12]1

Participants

4

Reactant 1

HCID 71255363HCID 71255363, compound

Product 1

HCID 71254580HCID 71254580, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of N-{[3-(dibenzylamino)oxetan-3-yl]methyl}-2-(5,5-difluoro-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)-6-methylquinazolin-4-amine (190 mg, 0.314 mmol) and trifluororacetic acid (1 drop) in methanol was stirred in the presence of palladium hydroxide on carbon (50 mg) at room temperature under hydrogen atmosphere overnight. The resulting mixture was filtered, concentrated in vacuo. The residue was purified by preparative HPLC to afford 32 mg of the product as a white solid (yield was 24%). MS obsd. (ESI+) [(M+H)+] 426, 1H NMR (400 MHz, CD3OD) δ ppm 7.696 (s, 1 H), 7.654-7.636 (d, J=7.2 Hz, 1 H), 7.607-7.588 (d, J=7.6 Hz, 1 H), 7.404-7.367 (m, 2 H), 7.341-7.283 (m, 2 H), 5.011 (s, 2 H), 4.683-4.626 (m, 2 H), 4.556-4.540 (d, J=6.4 Hz, 2 H), 4.335-4.307 (t, J=5.6 Hz, 2 H), 4.084 (s, 2 H), 5.528-2.432 (m, 2 H), 2.398 (s, 3 H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0d2e05d2f1614520b3186e50ccb128f9
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

Loading…