Diisopropylethylamine → HCID 67342802, compound

HRID 1257587Notes

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][CH:24]1[CH2:32][CH:31]2[CH:27]([CH2:28][C:29](=[O:44])[N:30]2[CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=2[O:42][CH3:43])[CH2:26][CH2:25]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:23][CH:24]4[CH2:32][CH:31]5[CH:27]([CH2:28][C:29](=[O:44])[N:30]5[CH2:33][C:34]5[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=5[O:42][CH3:43])[CH2:26][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: 120 °C

Procedure

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (137.2 mg, 0.4062 mmol), 6-amino-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one (107.8 mg, 0.3542 mmol), and diisopropylethylamine (0.10 mL, 0.57 mmol) in propan-2-ol (1.5 ml) was heated in a microwave reactor at 120° C. for 20 minutes. The solvent was evaporated in vacuo and then purified by column chromatography on silica gel (gradient: 0 to 100% ethyl acetate in dichloromethane) affording 152.3 mg (71%) of 6-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one. LCMS (Method E, ESI): RT=1.81 min, m+H=606.0.

Workup

customThe solvent was evaporated in vacuo
custompurified by column chromatography on silica gel (gradient: 0 to 100% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-646a8df44da240c1a0df83acbd885c54
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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