1-Octanol → HCID 117947828, compound

HRID 1499281Notes

Reaction equation

HRID 1499281 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:20][CH2:19][C:11]3([CH2:15][C@@H:14]([C:16]([OH:18])=[O:17])[NH:13][CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:21][C@H:22]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[N:34]2[CH:38]=[CH:37][C:36]([CH3:39])=[N:35]2)[C:23]([F:26])([F:25])[F:24])[N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:52](O)[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:20][CH2:19][C:11]3([CH2:12][NH:13][C@H:14]([C:16]([O:18][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[O:17])[CH2:15]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:21][C@H:22]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[N:34]2[CH:38]=[CH:37][C:36]([CH3:39])=[N:35]2)[C:23]([F:25])([F:24])[F:26])[N:3]=1

Participants

5

Reactant 3

HCID 9571-OctanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 117942361HCID 117942361, compound

Product 1

HCID 117947828HCID 117947828, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask equipped with a Dean Stark trap were added (2S)-8-[2-amino-6-[(1R)-1-[4-chloro-2-(3-methylpyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]-3,8-diazaspiro[4.5]decane-2-carboxylic acid (1 g, 1.78 mmol), toluene (25 mL), and p-toluene sulfonic acid monohydrate (336 mg, 1.77 mmol), and n-octanol (690 mg, 5.30 mmol). The reaction mixture was heated to reflux for 48 h, cooled to RT, and concentrated in vacuo. Purification on a 120 g Isco RediSep silica cartridge (CH2Cl2/MeOH/NH4OH) provided the title compound as a white solid.

Workup

  1. customTo a flask equipped with a Dean Stark trap
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 48 h
  4. concentrationconcentrated in vacuo
  5. customPurification on a 120 g Isco RediSep silica cartridge (CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-7f6970e819bb45b2969f44eacc9f85a3
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

Loading…