Dimethylformamide → HCID 178466762, compound

HRID 1383448Notes

Reaction equation

HRID 1383448 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([NH:20][C:21]#[N:22])=[N:9][C:10]2[CH:19]=[CH:18]C=[C:16]3[C:11]=2C=CC=[N:15]3)=[CH:4][CH:3]=1.[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1)[CH3:26].CN(C)C=O.C(N(CC)CC)C>O1CCCC1>[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([NH:9][C:10]3[CH:11]=[CH:16][N:15]=[CH:18][CH:19]=3)=[N:20][C:21]#[N:22])=[CH:23][CH:24]=2)=[O:36])=[CH:30][CH:29]=1)[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 122887Benzene, 1-ethoxy-4-isocyanato-HCID 178512242HCID 178512242, compound

Product 1

HCID 178466762HCID 178466762, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Amino-benzyl)-N′-cyano-N″-quinolin-5-yl-guanidine (100 mg, 0.380 mmol) and 1-ethoxy-4-isocyanato-benzene (61 mg,, 0.39 mmol) were dissolved in and mixture of N,N-dimethylformamide (2.0 mL).and tetrahydrofuran (1.0 mL). Triethylamine (0.060 mL, 0.390 mmol) was added. The reaction mixture was shaken at room temperature for 12 hours. The solvent was removed in vacuo to give the title compound (yield=85%). 1H NMR (DMSO-d6, ppm): 8.34 (br, s, 2H); 7.41-7.21 (m, 10H); 6.82-6.76 (m, 2H); 4.43 (s, 2H); 3.93 (dq, 2H); 1.28 (dt, 3H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-53a6d362362245f4902ab32638a00d79
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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