N-Aminomorpholine → HCID 58747011, compound

HRID 899314Notes

Reaction equation

HRID 899314 reaction equation
C[Al](C)C.[NH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C([O:14][C:15]([C:17]1[C:21]([NH2:22])=[C:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])[N:18]=1)=O)C>C(Cl)(Cl)Cl>[N:6]1([NH:5][C:15]([C:17]2[C:21]([NH2:22])=[C:20]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[N:19]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[N:18]=2)=[O:14])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 20315N-AminomorpholineHCID 16682925TrimethylaluminumHCID 58747008HCID 58747008, compound

Product 1

HCID 58747011HCID 58747011, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trimethylaluminum (2M solution in toluene, 625 microliters, 1.25 mmol) is added to a solution of 4-aminomorpholine (121 microliters, 1.25 mmol) in CHCl3 (3 ml) at room temperature. The reaction mixture was stirred for 1 h, then 4-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-2A-1a, 188 mg, 0.5 mmol) was added in one portion. The reaction mixture was stirred at 45° C. for 4 h, cooled to room temperature, and quenched with 1 M HCl (1 ml) (CAREFUL: gas evolution). The pH of the solution was adjusted to ˜13 using 25% KOH, at which point all solids went into solution. The aqueous solution was extracted with EtOAc (2×) and the combined organic solution was washed with saturated aqueous brine, dried, and concentrated under vacuum to give the product I-10A-1a as an amorphous solid (208 mg): MS 432.0 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 7.44-7.32 (m, 4H), 7.28-7.23 (m, 2H), 7.13-7.09 (m, 2H), 3.86 (m, 4H), 2.95 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred at 45° C. for 4 h
  2. customquenched with 1 M HCl (1 ml) (CAREFUL: gas evolution)
  3. extractionThe aqueous solution was extracted with EtOAc (2×)
  4. washthe combined organic solution was washed with saturated aqueous brine
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customto give the product

Sources & evidence

ORD record
ord-393612c77e534a9a84b2c6d0cbbe23e1
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

Loading…