tert-Butanol → HCID 58563674, compound

HRID 241944Notes

Reaction equation

HRID 241944 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=[C:9](C(O)=O)[CH:10]=[C:3]12.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[C:38]([O:42][C:19](=[O:28])[NH:16][C:9]1[CH:10]=[C:3]2[C:2](=[O:1])[CH2:7][CH2:6][CH2:5][N:4]2[N:8]=1)([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 226053224-oxo-4H,5H,6H,7H-pyrazolo[1,5-a]pyridine-2- carboxylic acid

Product 1

HCID 58563674HCID 58563674, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridine-2-carboxylic acid (2.56 g, 14.2 mmol, prepared according to EP1241170) in 160 mL dry toluene is added triethylamine (2.38 mL, 17.1 mmol) and diphenylphosphoryl azide (3.68 mL, 17.1 mmol) and the reaction mixture is stirred overnight at RT. Then tert-butanol (26.7 mL, 74.1 mmol) is added and the reaction is heated to 120° C. for 5 h. The solvents are removed under reduced pressure and the residue is purified by flash column chromatography (silica gel, 0-70% ethyl acetate in cyclohexane). Yield: 2.32 g. HPLC-MS: Rt=1.55 min, (M+H-56)+=196. 1H NMR (DMSO-d6): δ 9.8 (s, 1H), 6.7 (s, 1H), 4.2 (t, 2H), 2.6 (t, 2H), 2.3 (quint, 2H), 1.4 (s, 9H).

Workup

  1. temperaturethe reaction is heated to 120° C. for 5 h
  2. customThe solvents are removed under reduced pressure
  3. customthe residue is purified by flash column chromatography (silica gel, 0-70% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-8fc1b93c6591466885934fcbc3b18f93
Source dataset
uspto-grants-2014_02
Patent number
US08653097B2

Reaction notes

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