Cyanamide → HCID 178429747, compound

HRID 1840377Notes

Reaction equation

HRID 1840377 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[CH3:24])=[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][CH:20]=[C:19]([F:23])[C:18]=2[CH3:24])=[NH:39])=[C:10]([OH:25])[C:9]=1[S:33]([N:36]([CH3:37])[CH3:38])(=[O:35])=[O:34]

Participants

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 23447811HCID 23447811, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178429747HCID 178429747, compoundYield 44%

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-methyl-3-fluorophenyl)carbodiimide (320 mg, 0.64 mmol), cyanamide (108 mg, 2.56 mmol) and N,N-diisopropylethylamine (99 mg, 0.77 mmol) were reacted, followed by desilylation with Cesium fluoride (117 mg, 0.77 mmol) to form the desired product (120 mg, 44%). EI-MS m/z 426.2 (M+). 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 2.86 (s, 6H), 7.09 (m, 3H), 7.22 (m, 1H), 7.56 (d, 1H), 8.82 (s, 1H), 9.10 (s, 1H), 10.51 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-bb8f23338717454cbacd9af61e9821c9
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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