Hydrochloric Acid → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

HRID 2067199Notes

Reaction equation

HRID 2067199 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]2[N:26]=[N:27][N:28]([CH2:30][CH:31]3[CH2:35][O:34]C(C)(C)[O:32]3)[CH:29]=2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18].Cl.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]2[N:26]=[N:27][N:28]([CH2:30][CH:31]([OH:32])[CH2:35][OH:34])[CH:29]=2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11497523HCID 11497523, compound

Product 1

HCID 11555090[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 105 (535 mg, 1.16 mmol) in THF (6.0 mL) was added aqueous HCl (1M, 6 mL)) and the mixture was stirred for 24 h at RT. The reaction mixture was poured into a mixture of EtOAc/saturated NaHCO3. The aqueous phase was washed with more EtOAc. The collected organic phases were washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 2:98 to 10:90 as the eluent to afford the title compound as yellow foam. 13C NMR (DMSO-d6) δ 194.9, 158.7 (dd), 155.7 (dd), 149.3, 145.0, 139.8, 135.7, 133.7, 133.7, 131.6, 128.4, 127.1, 126.6, 126.5 (dd), 124.9, 124.2 (dd), 122.3, 114.8, 112.0 (dd), 111.8, 105.0 (dd), 70.3, 63.2, 53.0, 19.4

Workup

  1. washThe aqueous phase was washed with more EtOAc
  2. washThe collected organic phases were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-d22df564bb3a4125a4e96e71a6141f52
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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