Ammonium formate → HCID 15949402, compound

HRID 548681Notes

Reaction equation

HRID 548681 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[C:15]2[O:14][CH:13]([CH3:16])[N:12]([CH3:17])[C:11](=[O:18])[C:10]=2[CH:9]=[CH:8][C:7]=1[O:19][C:20]1[CH:21]=[C:22]([CH:32]=[C:33]([O:35][C@@H:36]([CH3:40])[CH2:37][O:38][CH3:39])[CH:34]=1)[C:23]([NH:25][C:26]1[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=1)=[O:24]>C(O)C.[Pd]>[CH3:16][CH:13]1[N:12]([CH3:17])[C:11](=[O:18])[C:10]2[CH:9]=[CH:8][C:7]([O:19][C:20]3[CH:21]=[C:22]([CH:32]=[C:33]([O:35][C@@H:36]([CH3:40])[CH2:37][O:38][CH3:39])[CH:34]=3)[C:23]([NH:25][C:26]3[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=3)=[O:24])=[CH:6][C:15]=2[O:14]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 15949316HCID 15949316, compound

Product 1

HCID 15949402HCID 15949402, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (122 mg, 1.9 mmol) was added in one portion to a solution of 3-[(8-chloro-2,3-dimethyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (100 mg, 0.19 mmol) in ethanol (3 mL). The reaction was blanketed with argon and 10% palladium on carbon (20 mg) was added. The mixture was heated to 140° C. for 10 minutes in a Smith Creator microwave after which complete conversion to desired product was observed. The reaction mixture was filtered through diatomaceous earth and the filter pad was washed well with ethyl acetate. The filtrate was evaporated in vacuo and the residue purified by column chromatography on silica, eluting with 60-100% ethyl acetate in hexanes, and then by chromatography on alumina, eluting with 20-60% ethyl acetate in hexanes, to afford the title compound as a colourless oil which foamed under high vacuum (50 mg).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-966c6920b7d348c8af6a7dbe3fd105e8
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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