Hydrochloric Acid → HCID 118390091, compound

HRID 1478058Notes

Reaction equation

HRID 1478058 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:11][CH2:10]2)[C:5]([Cl:27])=[CH:4][N:3]=1.[NH2:28][C:29]1[CH:30]=[N:31][N:32]([CH2:34][CH2:35][OH:36])[CH:33]=1.Cl.CCOC(C)=O>CC(O)C>[Cl:27][C:5]1[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][C:12]3([CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:18][CH2:19]3)[CH2:11][CH2:10]2)=[N:7][C:2]([NH:28][C:29]2[CH:30]=[N:31][N:32]([CH2:34][CH2:35][OH:36])[CH:33]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 118390013Tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 118390091HCID 118390091, compoundYield 81.85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate (501.5 mg, 1.21 mmol) and 2-(4-aminopyrazol-1-yl)ethanol (306.5 mg, 2.411 mmol) in propan-2-ol (6 mL) was added a solution of HCl in EtOAc (1 mL, 4 mmol). The mixture stirred in a sealed tube under the microwave radiation at 140° C. for 1 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/100 to 1/20 to 1/7) to give the product as a light yellow solid (500.0 mg, 0.9881 mmol, 81.85%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/100 to 1/20 to 1/7)

Sources & evidence

ORD record
ord-0e68b7ef941a4e5f83b1cb8fd701adc8
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…