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

HRID 1257756Notes

Reaction equation

Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]1.[C:9]1([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26](Cl)=[C:21]3[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C>C(O)C>[C:9]1([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]([NH:2][CH:3]4[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]4)=[C:21]3[CH:20]=[CH:19]2)(=[O:16])=[O:17])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-Amino-cyclopentanol hydrochloride (0.9 g, 5.9 mmol), 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (2.0 g, 5.9 mmol) and diisopropylethylamine (2.3 g, 17.7 mmol) in ethanol (100 mL) was stirred at 80° C. for 3 hours. The reaction mixture was purified by column chromatography (Hexanes/ethyl acetate=3:1) to give 2.6 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-8cf0498079bc4c2eb9b66c4228372beb
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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