Diisopropylethylamine → HCID 178504905, compound

HRID 1257726Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][S:9]([C@H:12]1[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]1)(=[O:11])=[O:10].[C:19]1([S:25]([N:28]2[C:32]3=[N:33][CH:34]=[C:35]([N+:38]([O-:40])=[O:39])[C:36](Cl)=[C:31]3[CH:30]=[CH:29]2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[C:19]1([S:25]([N:28]2[C:32]3=[N:33][CH:34]=[C:35]([N+:38]([O-:40])=[O:39])[C:36]([NH:18][C@H:15]4[CH2:16][CH2:17][C@H:12]([S:9]([CH3:8])(=[O:10])=[O:11])[CH2:13][CH2:14]4)=[C:31]3[CH:30]=[CH:29]2)(=[O:26])=[O:27])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of trans 4-methanesulfonyl-cyclohexylamine trifluoroacetic acid salt (383 mg, 1.32 mmol), 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (536 mg, 1.60 mmol), diisopropylethylamine (0.69 mL, 4.0 mmol) in propan-2-ol (5.5 mL), were heated at 120° C. for 10 minutes using microwave irradiation. The mixture was cooled to 0° C. and filtered, the resulting solid washed with propan-2-ol and ether, then dried under vacuum to give 588 mg (93%) of trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4-methanesulfonyl-cyclohexyl)-amine as a bright yellow solid. 1H NMR (400 MHz, CDCl3) δ: 9.11 (s, 1H), 8.99 (d, 1H), 8.20 (m, 2H), 7.64 (m, 2H), 7.53 (t, 2H), 6.66 (d, 1H), 3.95 (ddd, 1H), 2.95 (m, 1H), 2.91 (s, 3H), 2.40 (m, 4H), 1.85 (m, 2H), 1.52 (m, 2H).

Workup

custommicrowave irradiation
temperatureThe mixture was cooled to 0° C.
filtrationfiltered
washthe resulting solid washed with propan-2-ol and ether
customdried under vacuum

Sources & evidence

ORD record: ord-567f3549476047e2a81901db1d2ade80
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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