Diisopropylethylamine → 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol

HRID 1257754Notes

Reaction equation

[NH2:1][CH:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]1.[C:8]1([S:14]([N:17]2[C:21]3=[N:22][CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25](Cl)=[C:20]3[CH:19]=[CH:18]2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(C(C)C)CC)(C)C>C(O)C>[C:8]1([S:14]([N:17]2[C:21]3=[N:22][CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]([NH:1][CH:2]4[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]4)=[C:20]3[CH:19]=[CH:18]2)(=[O:15])=[O:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-Amino-cyclopentanol (about 2.5 g) in ethanol (50 mL) were added 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (7 g, 20.4 mmol) and diisopropylethylamine (DIPEA) (7.2 g, 60 mmol), then the reaction mixture was stirred at 80° C. for 3 hours. The reaction mixture was purified by column chromatography (Hexanes/ethyl acetate=3:1) to give 7.4 g (76%) of 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol. 1H NMR (400 MHz, CDCl3) δ: 9.56 (s, 1H), 9.54 (s, 1H), 8.19-8.16 (m, 2H), 7.62-7.56 (m, 4H), 6.82-6.81 (m, 1H), 4.56-4.50 (m, 2H), 2.25-1.96 (m, 6H).

Workup

customThe reaction mixture was purified by column chromatography (Hexanes/ethyl acetate=3:1)

Sources & evidence

ORD record: ord-70f0f1b57b8e4730b8edbbf2f2f4430e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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