HCID 57962468, compound → HCID 57962108, compound

HRID 541804Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:27])=[CH:4][N:3]=1>O.CO.C(O)(=O)C.[Fe]>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:16]([NH:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]2[C:5]([Cl:27])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:10]=1)=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}-3-nitrobenzamide (50.0 mg, 0.124 mmol) in water (0.09 mL), methanol (0.48 mL) and acetic acid (0.19 mL) was added iron (17 mg, 0.31 mmol) powder in small quantities. When the addition was completed, the mixture was stirred at 0° C. for 3 h, 3 eq additional iron powder was added. The mixture was filtered, and the cake was washed with MeOH/EtOAc. The brown filtrate was concentrated and diluted with H2O, and the aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as a light brown powder (32 mg, 69%). LCMS for C17H13Cl2N5O (M+H)+: m/z=374.0, 376.0. 1H NMR (400 MHz, CD3OD): δ 9.57 (s, 1H), 9.42 (s, 1H), 8.33 (s, 1H), 8.16 (s, 1H), 7.91 (s, 1H), 7.29 (dd, J=7.9, 7.6 Hz, 1H), 7.15 (d, J=7.9 Hz, 1H), 7.10-7.05 (m, 2H), 6.90 (dd, J=8.2, 0.9 Hz, 1H), 6.84-6.81 (m, 1H), 4.11 (s, 2H).

Workup

additionWhen the addition
filtrationThe mixture was filtered
washthe cake was washed with MeOH/EtOAc
concentrationThe brown filtrate was concentrated
additiondiluted with H2O
extractionthe aqueous layer was extracted with EtOAc three times
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-39a4e65f84fd4800ac64a9140f921812
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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