Cyanamide → HCID 178486148, compound

HRID 1840368Notes

Reaction equation

HRID 1840368 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[F:23])=[C:10]([O:24][Si](C(C)(C)C)(C)C)[C:9]=1[S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33].[N:38]#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[F:23])=[NH:38])=[C:10]([OH:24])[C:9]=1[S:32]([N:35]([CH3:36])[CH3:37])(=[O:34])=[O:33]

Participants

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 23447819HCID 23447819, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178486148HCID 178486148, compoundYield 40%

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-fluorophenyl)carbodiimide (350 mg, 0.72 mmol), cyanamide (121 mg, 2.88 mmol) and N,N-diisopropylethylamine (111 mg, 0.86 mmol) were reacted, followed by desilylation with Cesium fluoride (132 mg, 0.86 mmol) to form the desired product (120 mg, 40%). EI-MS m/z 412.2 (M+). 1H NMR (DMSO-d6) δ 2.86 (s, 6H), 7.20 (m, 2H), 7.27 (m, 2H), 7.40 (t, 1H), 7.52 (d, 1H), 9.06 (s, 1H), 9.20 (s, 1H), 10.51 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2f43855568e94d89840e1355de363fb7
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

Loading…