Acetic Acid → tert-Butyl [5-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)pyridin-3-yl]carbamate

HRID 541753Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[C:18]#[C:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[N:24][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.C(O)(=O)C>[Fe].O>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([C:18]#[C:19][C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[N:24][CH:25]=2)[CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)pyridin-3-yl]carbamate (1.60 g, 3.52 mmol), methanol (37 mL), acetic acid (7.3 mL), water (3.7 mL) and iron (905 mg, 16.2 mmol) was stirred at 60° C. for 3 h. The reaction mixture was filtered through a pad of celite and washed with ethyl acetate and extracted with ethyl acetate once. The combined organic solutions were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.40 g, 94%). LCMS calculated for C23H29N4O4(M+H)+: m/z=425.1.

Workup

filtrationThe reaction mixture was filtered through a pad of celite
washwashed with ethyl acetate
extractionextracted with ethyl acetate once
dry with materialThe combined organic solutions were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-8c805f6c10394f90bdfdc9360fbe2467
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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