1,4-Dioxane hydrochloride → HCID 118522497, compound

HRID 529782Notes

Reaction equation

HRID 529782 reaction equation
O1CCOCC1.Cl.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:48][CH:49]([F:51])[F:50])=[C:13]([C:15]2[C:19]([NH:20][C:21]([C:23]3[CH:24]=[N:25][N:26]4[CH:31]=[CH:30][CH:29]=[N:28][C:27]=34)=[O:22])=[CH:18][N:17]([CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][CH:37]([NH:40]C(=O)OC(C)(C)C)[CH2:36][CH2:35]3)[N:16]=2)[CH:14]=1>>[NH2:40][CH:37]1[CH2:38][CH2:39][N:34]([CH2:33][CH2:32][N:17]2[CH:18]=[C:19]([NH:20][C:21]([C:23]3[CH:24]=[N:25][N:26]4[CH:31]=[CH:30][CH:29]=[N:28][C:27]=34)=[O:22])[C:15]([C:13]3[CH:14]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=3[O:48][CH:49]([F:51])[F:50])=[N:16]2)[CH2:35][CH2:36]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118523182HCID 118523182, compound

Product 1

HCID 118522497HCID 118522497, compoundYield 98.7%

Procedure

Saturated HCl dioxane solution (15 mL) was added to tert-butyl N-[1-(2-[3-[5-chloro-2-(difluoromethoxy)phenyl]-4-[pyrazolo[1,5-a]pyrimidine-3-amido]-1H-pyrazol-1-yl]ethyl)piperidin-4-yl]carbamate (400 mg, 0.63 mmol). The resulting solution was stirred at room temperature overnight and concentrated under vacuum. The pH value of the remaining solution was adjusted to 8-9 with saturated aqueous Na2CO3. The resulting mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica eluting with MeOH/DCM (1:1) to afford 330 mg (98%) of N-[1-[2-(4-aminopiperidin-1-yl)ethyl]-3-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide as a yellow solid. LCMS (Method 28) [M+H]+=531.1, RT=0.49 min.

Workup

  1. concentrationconcentrated under vacuum
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe residue was purified by flash chromatography on silica eluting with MeOH/DCM (1:1)

Sources & evidence

ORD record
ord-1d0d0b6eed78456584e674d6046cd67e
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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