Tetrahydrofuran → HCID 66647793, compound

HRID 2428048Notes

Reaction equation

N/C(/C#N)=[C:3](\[NH:6][C:7]([NH:9][C@H:10]1CC[O:12][CH2:11]1)=O)/[C:4]#[N:5].[C:17]1([CH3:27])C(S(O)(=O)=O)=CC=CC=1.[N:28]([C@H:31]1[CH2:35][CH2:34][O:33][CH2:32]1)=[C:29]=[O:30].[NH2:36]/C(/C#N)=C(\N)/C#N.[O:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1>>[OH:44][C:48]1[CH:47]=[C:46]([C:7]2[N:6]=[C:3]3[C:4]([NH:5][C:29](=[O:30])[N:28]3[C@H:31]3[CH2:35][CH2:34][O:33][CH2:32]3)=[C:10]([C:11]([NH2:36])=[O:12])[N:9]=2)[CH:45]=[CH:17][CH:27]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 2723951Diaminomaleonitrile

HCID 86627734HCID 86627734, compound

HCID 86627735HCID 86627735, compound

Product 1

HCID 66647793HCID 66647793, compoundYield 39%

Procedure

(S,Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(tetrahydrofuran-3-yl)urea. (S)-3-Isocyanato tetrahydrofuran toluene sulfonate salt (0.825 g, 7.29 mmol) and diaminomaleonitrile (1.57 g, 14.59 mmol) were reacted according to General Procedure A in tetrahydrofuran (10 mL) and purified via reverse-phase preparative HPLC (0-10% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 35 min) to afford the title compound (0.636, 39%). MS (ESI) m/z 222.2 [M+1]+.

Workup

custompurified via reverse-phase preparative HPLC (0-10% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 35 min)

Sources & evidence

ORD record: ord-b3ee0ae74fa34a8a8108e83e9ace4916
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968556B2

Reaction notes

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