3-Chloro-4-[3-(trifluoromethyl)phenoxy]aniline → HCID 67520502, compound

HRID 1926148Notes

Reaction equation

HRID 1926148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][O:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.ClC1C2N(CCOCC3COC(C)(C)O3)C=CC=2N=CN=1.ClC1C=C(C=CC=1OC1C=CC=C(C(F)(F)F)C=1)N.Cl.C(OCC)(=O)C>C(OCC)(=O)C.C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][O:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1

Participants

7

Reactant 4

HCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 21866389Hydrogen chloride-ethyl acetateHCID 57597274HCID 57597274, compoundHCID 86615791HCID 86615791, compound

Product 1

HCID 67520502HCID 67520502, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}propane-1,2-diol was obtained by the reaction in the same manner as in Example 237 (iv) using 4-chloro-5-{2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidine (295 mg), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (359 mg) and isopropyl alcohol (6 mL). The obtained 3-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-O]pyrimidin-5-yl]ethoxy}propane-1,2-diol was dissolved in ethyl acetate (6 mL), 4N hydrochloric acid-ethyl acetate (0.2 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (360 mg) as a white powder.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9d63b720eeaf405bae11f54541a6797c
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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