Diisopropylethylamine → HCID 178511027, compound

HRID 1257713Notes

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.FC(F)(F)C(O)=O.[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([CH2:37][CH2:38][C:39]#[N:40])[CH2:33][CH2:32]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:30][C@H:31]4[CH2:36][CH2:35][C@H:34]([CH2:37][CH2:38][C:39]#[N:40])[CH2:33][CH2:32]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: 0 °C

Procedure

To a stirred suspension of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (3.17 g) in propan-2-ol (32 mL), trans 3-(4-amino-cyclohexyl)-propionitrile trifluoroacetic acid salt (2.75 g, 10.3 mmol) and diisopropylethylamine (4.09 mL, 23.5 mmol) were added. The mixture was stirred at reflux for 16 hours and then cooled to 0° C. The suspension was filtered, and the solid washed with propan-2-ol (×2) and ether, then air dried to afford 3.83 g (90%) of trans 3-[4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexyl]-propionitrile as a bright yellow solid. 1H NMR (400 MHz, CDCl3) δ: 9.10 (s, 1H), 8.99 (d, 1H), 8.19 (d, 2H), 7.66-7.59 (m, 2H), 7.52 (t, 2H), 6.67 (d, 1H), 3.91-3.80 (m, 1H), 2.40 (t, 2H), 2.24 (m, 2H), 1.96 (m, 2H), 1.66 (q, 2H), 1.55-1.39 m, 3H), 1.23-1.10 (m, 2H).

Workup

additionwere added
temperatureat reflux for 16 hours
filtrationThe suspension was filtered
washthe solid washed with propan-2-ol (×2) and ether
customair dried

Sources & evidence

ORD record: ord-1bca4d4665dd4e5d883338997eee485d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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