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

HRID 541886Notes

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

Into the reaction flask was added tert-butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)pyridin-3-yl]carbamate (1.6 g, 3.5 mmol), methanol (40 mL), acetic acid (7 mL), and water (4 mL). Then iron (0.90 g, 0.016 mol) powder was added. The reaction mixture was heated at 60° C. for 3 h. After filtration, the cake was rinsed with EtOAc. The filtrate was concentrated and the residue was diluted with NaHCO3 and EtOAc. After layer separation, the organic layer was dried, filtered and concentrated to give the desired product (1.4 g, 94%). LCMS for C23H29N4O4 (M+H)+: m/z=425.1.

Workup

filtrationAfter filtration
washthe cake was rinsed with EtOAc
concentrationThe filtrate was concentrated
additionthe residue was diluted with NaHCO3 and EtOAc
customAfter layer separation
customthe organic layer was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-03c50d952e4848e39fed90a4e135b9dc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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