Ammonia → HCID 59234767, compound

HRID 2040812Notes

Reaction equation

HRID 2040812 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:24]=[C:23]([CH3:25])[C:16]([O:17][CH2:18][CH:19]([OH:22])[CH2:20]O)=[C:15]([CH3:26])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1.CC[N:30](C(C)C)C(C)C.CS(Cl)(=O)=O.N>C1COCC1.CO>[NH2:30][CH2:20][CH:19]([OH:22])[CH2:18][O:17][C:16]1[C:15]([CH3:26])=[CH:14][C:13]([C:10]2[N:9]=[C:8]([C:6]3[CH:5]=[C:4]([CH3:27])[N:3]=[C:2]([Cl:1])[CH:7]=3)[O:12][N:11]=2)=[CH:24][C:23]=1[CH3:25]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59234746HCID 59234746, compound

Product 1

HCID 59234767HCID 59234767, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (RS)-3-{4-[5-(2-chloro-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol (134 mg, 0.345 mmol) in THF (5 mL), DIPEA (89 mg, 0.69 mmol) followed by methanesulfonylchloride (43 mg, 0.379 mmol) is added at 0° C. The mixture is stirred at it for 2 h before 7 M NH3 in MeOH (1.2 mL) is added. The mixture is stirred at 65° C. for 16 h before the solvent is removed in vacuo to give crude (RS)-1-amino-3-{4-[5-(2-chloro-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol as beige resin; LC-MS: tR=0.80 min, [M+1]+=388.96.

Workup

  1. additionis added at 0° C
  2. additionis added
  3. customis removed in vacuo

Sources & evidence

ORD record
ord-4477cd88cd3a4792a3088ac0abd90d18
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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