HCID 58557236, compound → HCID 58557876, compound

HRID 1969904Notes

Reaction equation

[CH2:1]([N:8]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:9]1[CH2:14][CH2:13][CH:12]([C:15](=O)[CH2:16][NH:17][C:18]2[N:19]=[C:20]3[CH:26]=[CH:25][N:24]([S:27]([C:30]4[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[C:21]3=[N:22][CH:23]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC#N>[CH2:1]([N:8]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][N:24]([S:27]([C:30]5[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=5)(=[O:29])=[O:28])[C:21]=4[N:22]=[CH:23][C:18]3=[N:17][CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-(4-(dibenzylamino)cyclohexyl)-2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)ethanone (5.8 g, 9.54 mmol) and PFPAA (23.7 g, 76 mmol) in MeCN (70 mL) was heated at about 50° C. for about 17 h. PFPAA (4.73 g, 15.2 mmol) was added and the reaction mixture was heated at about 60° C. for about 7 h and at ambient temperature for about 72 h. The solvent was removed under reduced pressure to yield N,N-dibenzyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclohexanamine (11.3 g crude, but assumed 5.6 g, 100%) as a foam: LC/MS (Table 1, Method b) Rt=3.03 and 3.09 min; MS m/z 590 (M+H)+.

Workup

additionPFPAA (4.73 g, 15.2 mmol) was added
temperaturethe reaction mixture was heated at about 60° C. for about 7 h and at ambient temperature for about 72 h
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-2f42127b767b45b2bb51cc2f6fac8c29
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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