Cyanamide → HCID 178486152, compound

HRID 1840388Notes

Reaction equation

[C:1](NC(N)=N)#[N:2].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[N:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[Cl:24])=[C:10]([O:25][Si](C(C)(C)C)(C)C)[C:9]=1[S:33]([N:36]([CH3:38])[CH3:37])(=[O:35])=[O:34].[N:39]#CN.C(N(CC)C(C)C)(C)C.[F-].[Cs+]>>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]([C:1]#[N:2])[C:15]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[Cl:24])=[NH:39])=[C:10]([OH:25])[C:9]=1[S:33]([N:36]([CH3:37])[CH3:38])(=[O:35])=[O:34]

Participants

Reactant 5

HCID 9864Cyanamide

HCID 25953Cesium fluoride

HCID 81531Diisopropylethylamine

HCID 23447853HCID 23447853, compound

HCID 178418324HCID 178418324, compound

Product 1

HCID 178486152HCID 178486152, compoundYield 50%

Procedure

Following the general procedure for cyanoguanidine formation outlined in example 12, N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]N′-(2-chloro4-fluorophenyl)carbodiimide (420 mg, 0.81 mmol), cyanamide (136 mg, 3.24 mmol) and N,N-diisopropylethylamine (126 mg, 1.62 mmol) were reacted, followed by desilylation with Cesium fluoride (148 mg, 1.62 mmol) to form the desired product (180 mg, 50%). EI-MS m/z 446.2 (M+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-778b99eb1dae4375a414a5021de79ab9
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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