Hydrochloric Acid → HCID 58574661, compound

HRID 1619432Notes

Reaction equation

HRID 1619432 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:3]1=2.CCN=C=NCCCN(C)C.Cl.[CH3:33][C:34]1[S:38][C:37]([NH2:39])=[N:36][CH:35]=1.Cl>C(Cl)Cl>[CH3:33][C:34]1[S:38][C:37]([NH:39][C:12]([C:10]2[CH:9]=[CH:8][N:7]3[C:2](=[O:1])[C:3]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:4]=4[N:5]=[C:6]3[CH:11]=2)=[O:14])=[N:36][CH:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3517702-Amino-5-methylthiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58574349HCID 58574349, compound

Product 1

HCID 58574661HCID 58574661, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the acid prepared from Example 28.1b and EDCI-HCl (80.2 mg, 0.42 mmol) in DCM (10 mL) was added 5-methylthiazol-2-amine (25.5 mg, 0.22 mmol). The mixture was stirred at room temperature for 10 min and then poured into 2 N HCl. The mixture was extracted with DCM (30 mL) and the organic layer was washed with aqueous NaHCO3, brine, dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by preparative HPLC to afford 5.5 mg of desired product. MS (ESI): 369 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.09-9.06 (d, J=7.38 Hz, 1H), 8.22 (s, 1H), 7.60-7.58 (d, J=6.57 Hz, 1H), 7.06 (t, J=5.4 Hz, 1H), 3.01-2.93 (m, 4H), 2.44 (s, 3H), 1.92-1.80 (m, 4H), 1.49 (broad, 4H). mGluR5 PAM EC50: +++++. Fold shift at 10 μM: +.

Workup

  1. extractionThe mixture was extracted with DCM (30 mL)
  2. washthe organic layer was washed with aqueous NaHCO3, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c3eec7c042ce4135be16f369ec1bf0ee
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…