Cyanamide → HCID 178486151, compound

HRID 1840373Notes

Reaction equation

HRID 1840373 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]=[C:19]([F:23])[C:18]=2[F: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.[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]=[C:19]([F:23])[C:18]=2[F:24])=[NH:39])=[C:10]([OH:25])[C:9]=1[S:33]([N:36]([CH3:37])[CH3:38])(=[O:35])=[O:34]

Participants

5

Reactant 4

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 23447837HCID 23447837, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178486151HCID 178486151, compoundYield 3.4%

Procedure

Following the general procedure for cyanoguanidine formation outlined in example 12, N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2,3-difluorophenyl)carbodiimide (340 mg, 0.68 mmol), cyanamide (114 mg, 2.72 mmol) and N,N-disopropylethylamine (106 mg, 0.82 mmol) were reacted, followed by desilylation with Cesium fluoride (124 mg, 0.82 mmol) to form the desired product (10 mg, 3.4%). EI-MS m/z 430.0 (M+). 1H NMR (DMSO-d6) δ 2.87 (s, 6H), 7.21 (m, 3H), 7.30 (m, 1H), 7.54 (d, 1H), 9.2 (s, 1H), 10.54 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d7f0644e007c4956b9cb8c2e0d06b799
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

Loading…