Stannous chloride dihydrate → HCID 22100636, compound

HRID 1458423Notes

Reaction equation

[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][N:14]2[C:18]3[C:19]([N+:37]([O-])=O)=[C:20]([O:23][CH:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:40]([CH3:42])[CH3:41])=[CH:5][CH:4]=1)#[N:2].O.O.[Sn](Cl)Cl>N1C=CC=CC=1>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][N:14]2[C:18]3[C:19]([NH2:37])=[C:20]([O:23][CH:24]4[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:28][CH2:29]4)[CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:40]([CH3:42])[CH3:41])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

1-(4-Cyanonaphth-1-yl)methyl-2-isopropyl-7-nitro-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)benzimidazole (12 g, 21 mmoL, 1 eq.) was dissolved in 400 mL dry pyridine and to this was added tin (II) chloride dihydrate (71 g, 315 mmoL, 15 eq.) which formed a finely divided suspension. The slurry was heated to 50° C. for 14 hours. The pyridine was stripped off, and the salts triturated in 1 L ethyl acetate. The salts were removed by filtration through Celite and the filtrate was concentrated to give a brown oil. Chromatography (3/2 ethyl acetate/hexanes) gave 7.6 g (67% yield) of 1-(4-cyanonaphth-1-yl)methyl-2-isopropyl-7-amino-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)benzimidazole as a tan foam.

Workup

customformed a finely divided suspension
customthe salts triturated in 1 L ethyl acetate
customThe salts were removed by filtration through Celite
concentrationthe filtrate was concentrated
customto give a brown oil

Sources & evidence

ORD record: ord-285df470a30341fb8bff0e0b67feb036
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849759

Reaction notes

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