Cyanamide → HCID 178461839, compound

HRID 2393288Notes

Reaction equation

HRID 2393288 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:38])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[C@H:10]([N:12]1[C:17](=[O:18])[C:16]2[S:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28](=[NH:31])OC)=[CH:24][CH:23]=3)=[CH:21][C:15]=2[N:14]=[CH:13]1)[CH3:11].[NH2:39][C:40]#[N:41]>CO>[C:40]([NH:41][C:28](=[NH:31])[C:25]1[CH:26]=[CH:27][C:22]([C:20]2[S:19][C:16]3[C:17](=[O:18])[N:12]([C@H:10]([CH3:11])[C@:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])([OH:38])[CH2:32][N:33]4[CH:37]=[N:36][CH:35]=[N:34]4)[CH:13]=[N:14][C:15]=3[CH:21]=2)=[CH:23][CH:24]=1)#[N:39]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 56984306HCID 56984306, compound

Product 1

HCID 178461839HCID 178461839, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1R,2R)-3-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-6-[4-[imino(methoxy)methyl]phenyl]thieno[3,2-d]pyrimidin-4(3H)-one (0.35 mg, 0.652 mmol) (obtained in example 63) and NH2CN (140 mg, 3.26 mmol) in MeOH (15 mL) was refluxed overnight. The solvent was removed by concentration and the residue was partitioned between CHCl3 and 10% NaHCO3 solution. The organic phase was separated, dried over Na2SO4, filtered, concentrated and purified by flash chromatography to give the title compound as a white solid: mp 275°-278° C.; 1H NMR (300 MHz, MeOH-d4) δ (MeOH) 8.61 (s, 1H, N=CH--N), 8.18 (s, 1H, triazole), 8.02 (d, J=8.5, 2H, arom), 7.95 (d, J=8.5, 2H, arom), 7.81 (s, 1H, thiophene), 7.66 (s, 1H, triazole), 7.43 (dt, Jt =6.5, Jd =9, 1H, arom), 7.08 (ddd, Jd =2.5, Jd =8.5, Jd =14, 1H, arom), 6.89 (dt, Jd =2.5, Jt =8.5, 1H, arom), 6.09 (q, J=7.3, 1H, MeCH), 5.09 (d, J=14.2, 1H, CH(H)), 4.19 (d, J=14.2, 1H, CH(H)), 1.33 (d, J=7.3, 3H, CHMe); [α]D =+43.0° (c 0.25, MeOH). Analysis calculated for C26H20F2N8O2S.H2O: C 55.31; H 3.93; N 19.85; S 5.68. Found: C 55.06; H 3.74; N 18.57; S 5.28.

Workup

  1. customThe solvent was removed by concentration
  2. customthe residue was partitioned between CHCl3 and 10% NaHCO3 solution
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8da340d0f55e4ab1928c44a40f8afa68
Source dataset
uspto-grants-1998_09
Patent number
US05807854

Reaction notes

Loading…