Cyanamide → HCID 178486146, compound

HRID 1840360Notes

Reaction equation

HRID 1840360 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][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])=[C:10]([O:27][Si](C(C)(C)C)(C)C)[C:9]=1[S:35]([N:38]([CH3:40])[CH3:39])(=[O:37])=[O:36].[N:41]#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][CH:20]=[CH:19][C:18]=2[C:23]([F:24])([F:26])[F:25])=[NH:41])=[C:10]([OH:27])[C:9]=1[S:35]([N:38]([CH3:39])[CH3:40])(=[O:36])=[O:37]

Participants

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 23447800HCID 23447800, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178486146HCID 178486146, compoundYield 37%

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-trifluoromethylphenyl)carbodiimide (250 mg, 0.47 mmol), cyanamide (79 mg, 1.88 mmol) and N,N-diisopropylethylamine (73 mg, 0.56 mmol) were reacted, followed by desilylation with Cesium fluoride (86 mg, 0.56 mmol) to form the desired product (80 mg, 37%). EI-MS m/z 462.0 (M+). 1H NMR (DMSO-d6) δ 2.86 (s, 6H), 7.14 (d, 1H), 7.53 (m, 2H), 7.59 (d, 1H), 7.75 (t, 1H), 7.77 (d, 1H), 8.91 (s, 1H), 9.28 (s, 1H), 10.53 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-80549bcaa13643c8a30292bb0085e617
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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