Diethyl Ether → HCID 68182901, compound

HRID 1615493Notes

Reaction equation

HRID 1615493 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]3[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[C:14]=3[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1.CCOCC.[NH4+].[Cl-]>O.O1CCCC1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:16]2([OH:20])[C:14]3[N:15]=[C:11]([C:10]4[C:2]([CH3:1])=[N:3][N:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=45)[S:12][C:13]=3[CH2:19][CH2:18][CH2:17]2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 68182985HCID 68182985, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 68182901HCID 68182901, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 250 mL round bottomed flask was placed 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-6,7-dihydro-1,3-benzothiazol-4(5H)-one (505.1 mg, 1.783 mmol) and tetrahydrofuran (50 mL). To the mixture was added a solution of 4-chlorophenylmagnesium bromide in ether (1M, 3.0 mL, 3.0 mmol) and the mixture was stirred for 4 hr at rt. To the mixture were added a saturated aqueous solution of NH4Cl (50 mL) and water (50 mL) and the resulting mixture was extracted with EtOAc (50 mL×2). The combined organic phases were dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain crude 4-(4-chlorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4,5,6,7-tetrahydro-1,3-benzothiazol-4-ol as a yellowish off-white crystalline solid which was used in the next step without further purification.

Workup

  1. customIn a 250 mL round bottomed flask was placed
  2. extractionthe resulting mixture was extracted with EtOAc (50 mL×2)
  3. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b4ef3d47f844fcc9bdb047d0eaeaa75
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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