Ammonium Chloride → {4-[2-Amino-4-(5-chloro-pyridin-2-ylcarbamoyl)-phenoxy]-phenyl}-carbamic acid tert-butyl ester

HRID 605214Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)=[CH:17][C:16]=2[N+:31]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.C(OCC)(=O)C.[Fe]>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)=[CH:17][C:16]=2[NH2:31])=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of the product of Example 199B (282 mg, 0.5816 mmol), iron powder (200 mg, 3.577 mmol), and ammonium chloride (204 mg, 3.809 mmol) in ethanol (8 mL) and water (4 mL) was heated at 80° C. for 45 minutes. After cooling to room temperature, the mixture was diluted with ethyl acetate (100 mL) and washed with water (2×50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound as a beige solid (250 mg, 94%).

Workup

temperatureAfter cooling to room temperature
washwashed with water (2×50 mL) and brine (50 mL)
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-89deecb5399e40a6ba749352df6d4c38
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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