Hydrochloric Acid → HCID 67003736, compound

HRID 2362652Notes

Reaction equation

HRID 2362652 reaction equation
[Cl:1][C:2]1[C:3]([C:30]2[S:34][C:33]([C:35]3([O:39][CH2:40][O:41][CH3:42])[CH2:38][CH2:37][CH2:36]3)=[N:32][CH:31]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=O)=[C:13]([F:19])[CH:12]=3)[N:8]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1.[F:43][CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1.Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl.CO>[Cl:1][C:2]1[C:3]([C:30]2[S:34][C:33]([C:35]3([O:39][CH2:40][O:41][CH3:42])[CH2:36][CH2:37][CH2:38]3)=[N:32][CH:31]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][N:47]4[CH2:48][CH2:49][CH:44]([F:43])[CH2:45][CH2:46]4)=[C:13]([F:19])[CH:12]=3)[N:8]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27591594-FluoropiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86659281HCID 86659281, compound

Product 1

HCID 67003736HCID 67003736, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 4 mL reaction vial was added 4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-fluorobenzaldehyde (Example 30A) (53 mg, 0.085 mmol), 4-fluoropiperidine, hydrochloric acid (35.46 mg, 0.255 mmol), methanol (0.5 ml), dichloromethane (0.5 ml), and a few drops of acetic acid. The reaction mixture was stirred at room temperature for 30 minutes, and sodium triacetoxyborohydride (53.82 mg, 0.255 mmol) was added. The reaction was stirred at room temperature overnight and then carefully quenched by addition of saturated sodium bicarbonate solution (about 400 μL) and dichloromethane (about 1 mL). The organic layer was collected, and the aqueous layer extracted with dichloromethane (2×1 mL). The combined organics were concentrated to give the title compound, which was used without further purification. MS APCI(+) m/z 713.42 [M+H]+.

Workup

  1. customTo a 4 mL reaction
  2. stirringThe reaction was stirred at room temperature overnight
  3. customcarefully quenched by addition of saturated sodium bicarbonate solution (about 400 μL) and dichloromethane (about 1 mL)
  4. customThe organic layer was collected
  5. extractionthe aqueous layer extracted with dichloromethane (2×1 mL)
  6. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-4b802224acdb4253bea5aee8fac6dc2f
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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