2-Amino-2-methyl-1-propanol → HCID 24760019, compound

HRID 1928390Notes

Reaction equation

HRID 1928390 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1.[NH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][OH:37]>C1COCC1.CCOC(C)=O>[OH:37][CH2:36][C:35]([NH:34][S:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:10]2[N:9]=[C:8]([C:6]3[CH:5]=[C:4]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=4)[CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:13]=[CH:12][CH:11]=2)[CH:15]=1)(=[O:22])=[O:21])([CH3:39])[CH3:38]

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 866154503-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonyl chloride

Product 1

HCID 24760019HCID 24760019, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonyl chloride (example I.2) (0.228 g, 0.47 mmol) by treatment with excess 2-amino-2-methyl-1-propanol in THF (10 mL) at 23° C. for 1 h. Diluted with EtOAc, washed with 5% citric acid, sat. NaHCO3-sol. and brine, dried organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with n-heptane/EtOAc followed by trituration with n-heptane/diethyl ether to give the title compound (0.158 g, 63%) as a white solid. MS (ISP) 541.9 [(M+H)+]; mp 171° C.

Workup

  1. washwashed with 5% citric acid, sat. NaHCO3-sol
  2. customRemoval of the solvent in vacuum
  3. waitleft a crude product, which
  4. customwas purified by silica gel column chromatography with n-heptane/EtOAc

Sources & evidence

ORD record
ord-9d9ee62f1d8945d698d419b58603e0b4
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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