Ethanol → HCID 118131394, compound

HRID 634501Notes

Reaction equation

HRID 634501 reaction equation
B(Br)(Br)Br.[ClH:5].[NH2:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]2[N:13]([CH:25]([C:27]3[O:28][C:29](=[O:47])[C:30]4[C:35]([C:36]=3[C:37]3[CH2:38][C:39]([CH3:46])([CH3:45])[NH:40][C:41]([CH3:44])([CH3:43])[CH:42]=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH3:26])[N:14]=[C:15]([C:16]3[CH:21]=[C:20]([O:22]C)[CH:19]=[C:18]([F:24])[CH:17]=3)[C:8]=12.CCO>C(Cl)Cl.C(O)=O.O.CC#N>[ClH:5].[NH2:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]2[N:13]([CH:25]([C:27]3[O:28][C:29](=[O:47])[C:30]4[C:35]([C:36]=3[C:37]3[CH2:38][C:39]([CH3:46])([CH3:45])[NH:40][C:41]([CH3:44])([CH3:43])[CH:42]=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH3:26])[N:14]=[C:15]([C:16]3[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([F:24])[CH:17]=3)[C:8]=12

Participants

7

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 118131387HCID 118131387, compound

Product 1

HCID 118131394HCID 118131394, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolvent2×HCID 6344DichloromethaneSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

1M Boron tribromide in DCM (2.1 ml, 2.100 mmol) was added to a solution of 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrochloride (226 mg, 0.373 mmol) in DCM (12 ml) and the resulting mixture was stirred at rt for 16 hrs. The suspension was slowly added at 0° C. to EtOH. The resulting mixture was concentrated under reduced pressure. Purification by RP-flash chromatography (Biotage 30 g C18 column, gradient elution from 100:0 to 60:40 A/B in 15 CV; A: water/MeCN 95/5+0.01% HCOOH, B: water/MeCN 5/95+0.01% HCOOH) yielded the title compound (168 mg, 0.284 mmol, 76% yield) as a pale yellow powder.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customPurification by RP-flash chromatography (Biotage 30 g
  3. washC18 column, gradient elution from 100:0 to 60:40 A/B in 15 CV

Sources & evidence

ORD record
ord-eb2657d99f6a480aa9d3ac0945638489
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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