Sulfuric Acid → HCID 58075723, compound

HRID 475921Notes

Reaction equation

HRID 475921 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:18][CH3:19])[C:5]2[C:10](=[O:11])[CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[Cl:20][C:21]1[N:22]=[CH:23][N:24]([C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=2[O:33][CH3:34])[CH:25]=1.S(=O)(=O)(O)O>C1COCC1>[Cl:20][C:21]1[N:22]=[CH:23][N:24]([C:26]2[CH:32]=[CH:31][C:29]([NH:30][C:2]3[N:3]=[C:4]([NH:18][CH3:19])[C:5]4[C:10](=[O:11])[CH2:9][CH:8]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:6]=4[N:7]=3)=[CH:28][C:27]=2[O:33][CH3:34])[CH:25]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 58075589HCID 58075589, compoundHCID 580757574-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline

Product 1

HCID 58075723HCID 58075723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-(methylamino)-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-5-one (Preparation AN) (7 mg) and 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline (Preparation A) (7 mg) in THF (0.2 mL) and sulfuric acid (4 mg) was heated at 85° C. for 12 h. THF was removed in vacuo, and the residue was purified by reverse phase preparative to give the title compound (as its TFA salt) as a yellowish oil (9 mg). LC-MS (M+H)+=461.12. 1HNMR (500 MHz, CD3OD) δ ppm 7.80 (m), 7.1-7.4 (m), 4.50 (1H, m), 3.25 (1H, m), 2.56 (1H, m), 3.50 (3H, s), and 3.19 (3H, s).

Workup

  1. customTHF was removed in vacuo
  2. customthe residue was purified by reverse phase preparative

Sources & evidence

ORD record
ord-c2f8ee7c5cef46b5881e31b20cdb9cd1
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

Loading…