Formaldehyde → HCID 44816057, compound

HRID 1671303Notes

Reaction equation

HRID 1671303 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:18]=[C:17]([CH3:19])[CH:16]=[C:11]2[O:12][C:13]=1[CH2:14][CH3:15].[CH2:20]([NH:23][CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22].[CH2:27]=O>CC(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:18]=[C:17]([CH3:19])[C:16]([CH2:27][N:23]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:21][CH3:22])=[C:11]2[O:12][C:13]=1[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8902DipropylamineHCID 59186147HCID 59186147, compound

Product 1

HCID 44816057HCID 44816057, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(2,4-dichloro-phenyl)-2-ethyl-6-methyl-pyrazolo[5,1-b]oxazole (Intermediate HO)(30 mg, 0.10 mmol, 1 eq.) and dipropylamine (0.042 ml, 0.31 mmol, 3 eq.) in AcOH (0.3 ml) is added formaldehyde (36.5% in water, 0.025 ml, 0.31 mmol, 3 eq.) at RT. The reaction mixture is heated at 50° C. for 2 h then cooled to RT and directly subjected to purification by reverse phase prep-HPLC (Waters system) to yield the title compound (TFA salt) as a colourless resin. HPLC: AtRet=1.89; MS: m/z 408.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 0.96 (t, 6H), 1.22 (t, 3H), 1.73-1.83 (m, 4H), 2.30 (s, 3H), 2.68 (q, 2H), 2.96-3.05 (m, 4H), 4.34 (m, 2H), 7.68 (m, 2H), 7.93 (m, 1H).

Workup

  1. temperaturethen cooled to RT
  2. customdirectly subjected to purification by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record
ord-9de1938a7476493297c3259b4a938e29
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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