Hydrochloric Acid → HCID 90067629, compound

HRID 1057059Notes

Reaction equation

HRID 1057059 reaction equation
[F:1][C:2]1([F:35])[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[CH:10]=[C:9]([NH:24][C:25]3[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=3)[N:8]=2)[CH2:3]1.O1CCOCC1.Cl.C([O-])(O)=O.[Na+]>>[NH:15]1[CH2:14][CH:13]([C:11]2[CH:12]=[C:7]([N:4]3[CH2:5][CH2:6][C:2]([F:35])([F:1])[CH2:3]3)[N:8]=[C:9]([NH:24][C:25]3[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[CH:27][N:26]=3)[CH:10]=2)[CH2:16]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 516892Sodium BicarbonateHCID 90067689HCID 90067689, compound

Product 1

HCID 90067629HCID 90067629, compound

Procedure

To a solution of tert-butyl 3-[2-(3,3-difluoropyrrolidin-1-yl)-6-[[4-(trifluoromethyl)-2-pyridyl]amino]-4-pyridyl]azetidine-1-carboxylate (1-c, 918 mg, 1.562 mmol) in dioxane (6.0 ml, 70.30 mmol) was added hydrogen chloride (4.0 mol/l) in dioxane (16.0 mL, 40 equiv., 62.49 mmol), and the reaction was kept at 25° C. for 4 h. The reaction was neutralized by NaHCO3 to pH 9, and the aqueous layer was extracted by EtOAc. After evaporation of the organic layer, the crude was used without further purification. LCMS: m/z 400 (M+H).

Workup

  1. extractionthe aqueous layer was extracted by EtOAc
  2. customAfter evaporation of the organic layer
  3. customthe crude was used without further purification

Sources & evidence

ORD record
ord-7a6ca40545f54765b3084c78f56f948b
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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