Hydrochloric Acid → HCID 178506055, compound

HRID 712974Notes

Reaction equation

HRID 712974 reaction equation
[F:1][CH:2]([F:26])[CH2:3][N:4]1[CH2:21][CH:20]([C:22](=O)[C:23]#[CH:24])[O:19][C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5]1.[NH2:27][NH2:28].Cl>C(O)C>[F:1][CH:2]([F:26])[CH2:3][N:4]1[CH2:21][CH:20]([C:22]2[CH:23]=[CH:24][NH:28][N:27]=2)[O:19][C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 89051740Tert-butyl 8-(2,2-difluoroethyl)-10-prop-2-ynoyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 178506055HCID 178506055, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of tert-butyl 8-(2,2-difluoroethyl)-10-prop-2-ynoyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (25 mg, 0.07 mmol), hydrazine (42 μL, 1.34 mmol) and ethanol (0.5 mL) was stirred for 1 hour at room temperature. The solution was concentrated in vacuo to give the crude pyrazole as a yellow oil. HCl (400 μL of 4 M in dioxane, 1.60 mmol) followed by ethanol (0.2 mL) was added and the reaction mixture was stirred for 15 minutes at room temperature. The reaction mixture was concentrated in vacuo to give 8-(2,2-difluoroethyl)-10-(1H-pyrazol-3-yl)-11-oxa-3,8-diazaspiro[5.5]undecane as a gummy yellow solid. ESI-MS m/z calc. 286.2. found 287.1 (M+1)+; Retention time: 0.32 minutes (3 min run).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give the crude pyrazole as a yellow oil
  3. additionwas added
  4. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e500ae0f2ba04c0ab586783b42db2b4d
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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