Ammonium formate → HCID 178481130, compound

HRID 548740Notes

Reaction equation

HRID 548740 reaction equation
Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([C:28]([NH:30][C:31]2[CH:35]=[CH:34][N:33](C(OC(C)(C)C)=O)[N:32]=2)=[O:29])[CH:19]=[C:20]([O:22][C@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[CH:21]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:13][N:8]1[C:7](=[O:14])[C:6]2[CH:5]=[CH:4][C:3]([O:15][C:16]3[CH:17]=[C:18]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][O:25][CH2:24]4)[CH:21]=3)[C:28]([NH:30][C:31]3[CH:35]=[CH:34][NH:33][N:32]=3)=[O:29])=[CH:2][C:12]=2[O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57663212HCID 57663212, compound

Product 1

HCID 178481130HCID 178481130, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

1,1-Dimethylethyl 3-[({3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate (107 mg, 0.17 mmol) was dissolved in ethanol (4 mL) and ammonium formate (125 mg, 1.7 mmol) was added in one portion. The reaction was blanketed with argon and 10% palladium on charcoal (30 mg) was added. The mixture was heated to 140° C. for 15 minutes in a microwave reactor then the mixture filtered through diatomaceous earth, washed well with ethanol and evaporated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0-10% methanol in DCM, to give the desired compound as a white foam (60 mg). 1H NMR δ (CDCl3): 2.12-2.29 (2H, m), 3.21 (3H, s), 3.57-3.60 (2H, m), 3.88-4.02 (5H, m), 4.41 (2H, t), 4.99 (1H, m), 6.58 (1H, d), 6.70-6.75 (1H, m), 6.76-6.79 (1H, m), 6.81 (1H, d), 7.19 (1H, s), 7.27 (1H, s), 7.51 (1H, d), 7.85 (1H, d), 9.23 (1H, s); m/z 465 (M+H)+, 463 (M−H)−

Workup

  1. additionwas added
  2. filtrationthe mixture filtered through diatomaceous earth
  3. washwashed well with ethanol
  4. customevaporated in vacuo
  5. customThe crude product was chromatographed on silica
  6. washeluting with a gradient of 0-10% methanol in DCM

Sources & evidence

ORD record
ord-7c99774f553744cbb1bef2c973b9898b
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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