Hydrochloric Acid → HCID 86680108, compound

HRID 1915901Notes

Reaction equation

HRID 1915901 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH:17][C:18]2[CH:19]=[N:20][N:21]([CH3:40])[C:22]=2[N:23]2[CH2:29][C:28]([F:31])([F:30])[CH2:27][CH:26]([NH:32]C(=O)OC(C)(C)C)[CH2:25][CH2:24]2)=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[N:6][CH:7]=1.Cl>O1CCOCC1>[NH2:1][C:2]1[C:3]([C:15]([NH:17][C:18]2[CH:19]=[N:20][N:21]([CH3:40])[C:22]=2[N:23]2[CH2:24][CH2:25][CH:26]([NH2:32])[CH2:27][C:28]([F:31])([F:30])[CH2:29]2)=[O:16])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86680109HCID 86680109, compound

Product 1

HCID 86680108HCID 86680108, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 1-(4-(5-amino-2-(2-fluorophenyl)pyrimidine-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-6,6-difluoroazepan-4-ylcarbamate (157 mg) was stirred with 4N HCl in dioxane (6 mL) at room temperature for 1 h. The reaction mixture was concentrated to dryness, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate 3×. Combined organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified on reversed phase HPLC to give 237. MS (ESI) m/z: 461.1 [M+H+].

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionextracted with ethyl acetate 3×
  3. dry with materialCombined organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified on reversed phase HPLC

Sources & evidence

ORD record
ord-6bf27faae6e64efa837bdef6b7bd8be1
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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