p-Toluenesulfonic acid → HCID 9952234, compound

HRID 1838402Notes

Reaction equation

[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[N:15]=[C:10]3[CH:9]=[C:8]2[C:20](=[S:22])[NH2:21])=[CH:4][CH:3]=1.CO[CH:27](OC)[CH2:28]Br.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:17])=[O:18])[N:15]=[C:10]3[CH:9]=[C:8]2[C:20]2[S:22][CH:27]=[CH:28][N:21]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-(4-fluorobenzyl)-2-methanesulfonyl-5H-pyrrolo[2,3-b]pyrazine-6-thioamide (90 mg), bromoacetaldehyde dimethylacetal (0.06 ml), p-toluenesulfonic acid (4 mg) and acetic acid (1 ml) was stirred at 100° C. for 1.5 hours. The reaction solution was separated using silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the desired product (30 mg).

Workup

customThe reaction solution was separated

Sources & evidence

ORD record: ord-4e934ef0e60843f1b6ad4f0f57b291f6
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673797B1

Reaction notes

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