Hydrochloric Acid → HCID 463714, compound

HRID 2393289Notes

Reaction equation

HRID 2393289 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])[O:29]C)=[CH:24][CH:23]=3)=[CH:21][C:15]=2[N:14]=[CH:13]1)[CH3:11].Cl>CO>[NH2:31][C:28]([C:25]1[CH:24]=[CH:23][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:27][CH:26]=1)=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56984306HCID 56984306, compound

Product 1

HCID 463714HCID 463714, 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 g, 0.652 mmol) (obtained in example 63) and 1N HCl (2 mL) in MeOH (15 mL) was allowed to react at room temperature 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 280°-285° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.61 (s, 1H, N=CH--N), 7.92 (d, Jt =8.4, 2H, arom), 7.81 (d, Jt =8.4, 2H, arom), 7.78 (s, 1H, triazole), 7.74 (s, 1H, triazole, 7.63 (s, 1H, thiophene), 7.49 (dt, Jd =6.4, Jt =8.8, 1H, arom), 6.9-6.7 (m, 2H, arom), 6.2-5.5 (broad signal, 2H, NH2), 5.98 (dq, Jd =1.6, Jq =7.3, 1H, MeCH), 5.56 (d, J=1.6, 1H, OH), 5.20 (d, J=14.2, 1H, CH(H)), 4.03 (d, J=14.2, 1H, CH(H)), 1.32 (d, J=7.3, 3H, CHMe); MS 299 (N-ethylheterocycle, C15H13N3O2 S), 224 (Tr--CH2COHAr, C10H8F2N3O); [α]D =+63.6° (c 1, MeOH).

Workup

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

Sources & evidence

ORD record
ord-a1c091ebe4a3463d80fca84eb2bc2cbb
Source dataset
uspto-grants-1998_09
Patent number
US05807854

Reaction notes

Loading…