Cyclohexylamine → (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-cyclohexyl-amine

HRID 1257589Notes

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.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(C(C)C)CC)(C)C>CC(O)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:29][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]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: 80 °C

Procedure

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (10 g, 29.6 mmol), cyclohexyl amine (3.4 ml, 30.0 mmol), diisopropylethylamine (11 ml, 65.0 mmol) in propan-2-ol (150 ml) was heated at 80° C. for 14 h. The mixture was then cooled to 25° C. and stirred for 6 h. The resulting yellow solid was collected by vacuum filtration, washed with propan-2-ol (1×30 ml), and was air-dried to afford (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-cyclohexyl-amine (10.45 g, 90%). LCMS (Method G, ESI): RT=1.33 min, m+H=401.2; 1H NMR (400 MHz, DMSO) δ 8.93 (s, 1H), 8.91 (s, 1H), 8.13 (d, J=7.6 Hz, 2H), 7.82 (d, J=4.1 Hz, 1H), 7.77 (t, J=7.4 Hz, 1H), 7.66 (t, J=7.8 Hz, 2H), 6.99 (d, J=4.2 Hz, 1H), 4.12-4.01 (m, 1H), 2.02-1.93 (m, 2H), 1.76-1.54 (m, 3H), 1.55-1.38 (m, 4H), 1.33-1.20 (m, 1H).

Workup

temperatureThe mixture was then cooled to 25° C.
filtrationThe resulting yellow solid was collected by vacuum filtration
washwashed with propan-2-ol (1×30 ml)
customwas air-dried

Sources & evidence

ORD record: ord-15f698a5600645cdad44308272fcf173
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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