Triethylamine → HCID 15949312, compound

HRID 548672Notes

Reaction equation

HRID 548672 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:19]2[O:18][CH2:17][CH2:16][N:15]([CH3:20])[C:14](=[O:21])[C:13]=2[CH:12]=[CH:11][C:10]=1[O:22][C:23]1[CH:24]=[C:25]([CH:35]=[C:36]([O:38][C@@H:39]([CH3:42])[CH2:40][OH:41])[CH:37]=1)[C:26]([NH:28][C:29]1[CH:33]=[CH:32][N:31]([CH3:34])[N:30]=1)=[O:27]>[Pd].C1COCC1.C(O)C>[OH:41][CH2:40][C@H:39]([CH3:42])[O:38][C:36]1[CH:35]=[C:25]([CH:24]=[C:23]([O:22][C:10]2[CH:11]=[CH:12][C:13]3[C:14](=[O:21])[N:15]([CH3:20])[CH2:16][CH2:17][O:18][C:19]=3[CH:9]=2)[CH:37]=1)[C:26]([NH:28][C:29]1[CH:33]=[CH:32][N:31]([CH3:34])[N:30]=1)=[O:27]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 15949217HCID 15949217, compound

Product 1

HCID 15949312HCID 15949312, compoundYield 41.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon (30 mg) and triethylamine (2.0 mL) were added to a solution of 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (160 mg; 0.32 mmol) in dry THF (4 mL) and dry ethanol (4 mL) under argon. The reaction was degassed and placed under a hydrogen balloon and stirred for 24 hours at RT. The mixture was filtered through diatomaceous earth and the filtrate was evaporated. Purification by column chromatography on silica, eluting with 0-5% methanol in DCM, yielded a colourless oil which solidified under vacuum to give the title compound as a white foam (62 mg, 33%). 1H NMR δ (CDCl3): 1.23 (d, 3H), 2.00 (dd, 1H), 3.14 (s, 3H), 3.51 (t, 2H), 3.64-3.71 (m, 2H), 3.73 (s, 3H), 4.34 (t, 2H), 4.46 (dq, 1H), 6.51 (d, 1H), 6.69 (d, 1H), 6.70-6.72 (m, 2H), 7.02 (t, 1H), 7.18 (t, 1H), 7.21 (d, 1H), 7.81 (d, 1H), 8.38 (s, 1H) m/z 467 (M+H)+ 465 (M−H)−

Workup

  1. customThe reaction was degassed
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customthe filtrate was evaporated
  4. customPurification by column chromatography on silica
  5. washeluting with 0-5% methanol in DCM
  6. customyielded a colourless oil which

Sources & evidence

ORD record
ord-f05a8ee63ae64d478d73f03ef9f77c63
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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