Hydrochloric Acid → HCID 86672469, compound

HRID 72884Notes

Reaction equation

HRID 72884 reaction equation
[F:1][CH:2]([F:28])[CH2:3][N:4]1[CH2:21][CH:20]([C:22]2[NH:26][N:25]=[CH:24][C:23]=2[CH3:27])[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.Cl.Cl.FC(F)CN1CC(C2NN=CC=2C)OC2(CCNCC2)C1>C(O)C>[F:28][CH:2]([F:1])[CH2:3][N:4]1[CH2:21][CH:20]([C:22]2[NH:26][N:25]=[CH:24][C:23]=2[CH3:27])[O:19][C:6]2([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86672470tert-butyl 8-(2,2-difluoroethyl)-10-(4-methyl-1H-pyrazol-5-yl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylateHCID 86672471HCID 86672471, compound

Product 1

HCID 86672469HCID 86672469, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl 8-(2,2-difluoroethyl)-10-(4-methyl-1H-pyrazol-5-yl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (80 mg, 0.20 mmol) in ethanol (0.2 mL) was added HCl (500 μL of 4 M in dioxane, 2.00 mmol) and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated in vacuo to give, 8-(2,2-difluoroethyl)-10-(4-methyl-1H-pyrazol-5-yl)-11-oxa-3,8-diazaspiro[5.5]undecane hydrochloride salt as a yellow solid. ESI-MS m/z calc. 300.2. Found 301.3 (M+1)+; Retention time: 0.48 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 8.74 (s, 2H), 7.45 (s, 1H), 6.49-6.08 (m, 1H), 5.76 (s, 1H), 4.88 (d, J=9.6 Hz, 1H), 3.21-2.57 (m, 10H), 2.06 (s, 3H), 1.81-1.56 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give
  3. customRetention time: 0.48 minutes (3 min run)

Sources & evidence

ORD record
ord-b036d4e9834447999104a74315428f1d
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

Loading…