Cyanamide → HCID 178486150, compound

HRID 1840384Notes

Reaction equation

HRID 1840384 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[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][CH:20]=[C:19]([F:23])[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

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 23447838HCID 23447838, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178486150HCID 178486150, compoundYield 39%

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-chloro-3-fluorophenyl)carbodiimide (360 mg, 0.7 mmol), cyanamide (118 mg, 2.8 mmol) and N,N-diisopropylethylamine (109 mg, 0.84 mmol) were reacted, followed by desilylation with Cesium fluoride (128 mg, 0.84 mmol) to form the desired product (120 mg, 39%). LC-MS m/z 446.2 (M+). 1H NMR (DMSO-d6) δ 2.86 (s, 6H), 7.20 (d, 1H), 7.33 (t, 1H), 7.40 (m,2H), 7.58 (d, 1H), 9.11 (s, 1H), 9.31 (s, 1H), 10.52 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d6fa0858edb2428e92cbb78fdd98f154
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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