Diethyl Ether → HCID 68642184, compound

HRID 403524Notes

Reaction equation

HRID 403524 reaction equation
Cl.[F:2][C:3]1[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[C:10]([C:11]2[CH:15]=[CH:14][O:13][N:12]=2)=[CH:9][C:8]([C:16]2[N:21]=[C:20]([NH2:22])[C:19]([NH2:23])=[CH:18][N:17]=2)=[N:7]1.ClCCl.[CH2:31]([O:33]CC)[CH3:32]>C(O)(=O)C>[NH2:22][C:20]1[C:19]([NH:23][C:31](=[O:33])[CH3:32])=[CH:18][N:17]=[C:16]([C:8]2[CH:9]=[C:10]([C:11]3[CH:15]=[CH:14][O:13][N:12]=3)[N:6]([CH2:5][C:4]3[CH:24]=[CH:25][CH:26]=[CH:27][C:3]=3[F:2])[N:7]=2)[N:21]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 66634026HCID 66634026, compound

Product 1

HCID 68642184HCID 68642184, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidine-4,5-diamine hydrochloride (I-107) (30 mg, 0.077 mmol) in acetic acid (2 mL) was heated to 110° C. for 18 h. After cooling to room temperature, the solution was partitioned between ethyl actetate (50 mL) and saturated aqueous sodium carbonate. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organics were dried over MgSO4, filtered, and the solvent was removed in vacuo to give the crude product as a tan residue. Dichloromethane (3 mL) and diethyl ether (5 mL) were added, and the resulting white solid was filtered and washed with additional diethyl ether ether to give N-(4-amino-2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidin-5-yl)acetamide (24 mg, 0.061 mmol, 79% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.42 (d, 1H), 8.26 (s, 1H), 7.66 (br s, 1H), 7.34 (s, 1H), 7.18-7.13 (m, 1H), 7.01-6.96 (s, 1H), 6.92 (t, 1H), 6.77 (t, 1H), 6.56 (d, 1H), 5.96 (s, 2H), 5.57 (br s, 2H), 2.12 (s, 3H).

Workup

  1. customthe solution was partitioned between ethyl actetate (50 mL) and saturated aqueous sodium carbonate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto give the crude product as a tan residue
  8. filtrationthe resulting white solid was filtered
  9. washwashed with additional diethyl ether ether

Sources & evidence

ORD record
ord-780ff5d5ef164ec9af9e88e42683a881
Source dataset
uspto-grants-2014_06
Patent number
US08748442B2

Reaction notes

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