(1R,3R)-3-aminocyclohexanol → (1R,3R)-3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino) cyclohexanol

HRID 1257743Notes

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][C@@H:26]([OH:30])[CH2:25]1>C(O)(C)C>[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]([NH:23][C@@H:24]4[CH2:29][CH2:28][CH2:27][C@@H:26]([OH:30])[CH2:25]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 82 °C

Procedure

A stirred suspension of 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (2.92 g, 8.65 mmol) and (1R,3R)-3-Amino-cyclohexanol (1.00 g, 8.68 mmol) in isopropyl alcohol (30 ml) was treated with N,N-diisoppropylethylamine (2.27 ml, 13 mmol) and heated at 82° C. overnight. LC/MS shows reaction complete. Reaction cooled to room temperature and used as is for the next step. LCMS (Method M, ESI): RT=2.52 min, m+H=417.3; 1H).

Workup

additionwas treated with N,N-diisoppropylethylamine (2.27 ml, 13 mmol)
customreaction complete
customReaction
temperaturecooled to room temperature

Sources & evidence

ORD record: ord-16a86002fc534c5e9266b1106375b2ea
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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