Hydrochloric Acid → HCID 66576407, compound

HRID 1775596Notes

Reaction equation

HRID 1775596 reaction equation
[N:1]([O-])=O.[Na+].[ClH:5].[NH2:6][C:7]1[N:11]([CH2:12][CH2:13]O)[N:10]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:8]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH2:30]>C(Cl)Cl>[Cl:5][C:22]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:1][N:6]=[C:7]2[N:11]([CH2:12][CH2:13][OH:30])[N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[C:8]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23668193Sodium NitriteHCID 70983357HCID 70983357, compound

Product 1

HCID 66576407HCID 66576407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Sodium nitrite (555 mg, 8.04 mmol) was added portionwise to a cooled (cooling bath −10° C.) stirred solution of conc. HCl (11.7 mL). After 15 minutes, 2-(5-amino-3-(3-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol (860 mg, 2.68 mmol) was added portionwise and the reaction mixture was allowed to warm to room temperature over 90 min. Water and CH2Cl2 were added to the reaction mixture. The aqueous phase was extracted with CH2Cl2 (×4) and the organic phases combined, dried over MgSO4, filtered and evaporated the crude material was purified using chromatography (silica gel, gradient 0 to 50% ethyl acetate/isohexane) followed by preparative HPLC yielding Compound 94 as a white solid (40 mg).

Workup

  1. temperaturea cooled
  2. temperatureto warm to room temperature over 90 min
  3. extractionThe aqueous phase was extracted with CH2Cl2 (×4)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated the crude material
  7. customwas purified

Sources & evidence

ORD record
ord-67e7dd722d234561a9823b3b6579099c
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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