Diisopropylethylamine → HCID 67345038, compound

HRID 1257579Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.6769 g, 2.004 mmol), (S)-3-amino-1-Boc-piperidine (0.4269 g, 2.132 mmol), and diisopropylethylamine (0.45 mL, 2.6 mmol) in propan-2-ol (12 ml) was heated in a microwave reactor at 110° C. for 20 minutes. The solvent was evaporated in vacuo and then purified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate in heptanes) affording 853.7 mg (85%) of (S)-3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester. LCMS (Method F, ESI): RT=1.19 min, m+H=502.3.

Workup

customThe solvent was evaporated in vacuo
custompurified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate in heptanes)

Sources & evidence

ORD record: ord-61cd0d8c4032468baf24f84bc5b5a945
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

Loading…