Dimethylformamide → HCID 89546935, compound

HRID 2171264Notes

Reaction equation

HRID 2171264 reaction equation
CCN(C(C)C)C(C)C.CN(C=O)C.[NH2:15][C@H:16]([CH:27]1[CH2:30][CH2:29][CH2:28]1)[C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18].[Cl:31][C:32]1[N:39]=[C:38](Cl)[C:37]([F:41])=[CH:36][C:33]=1[C:34]#[N:35]>O>[Cl:31][C:32]1[N:39]=[C:38]([NH:15][C@H:16]([CH:27]2[CH2:28][CH2:29][CH2:30]2)[C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH3:18])[C:37]([F:41])=[CH:36][C:33]=1[C:34]#[N:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 89546936HCID 89546936, compound

Product 1

HCID 89546935HCID 89546935, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIPEA (17 ml) was added to a DMF (30 ml) solution containing tert-butyl ((1R,2S)-1-amino-1-cyclobutylpropan-2-yl)carbamate and 2,6-dichloro-5-fluoronicotinonitrile (16.2 g) obtained in the 5th step at 70° C., followed by stirring for 3 hours. The reaction solution was adjusted to room temperature and water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and the organic layers were dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 1:1). A white solid of tert-butyl ((1R,2S)-1-((6-chloro-5-cyano-3-fluoropyridin-2-yl)amino)-1-cyclobutylpropan-2-yl)carbamate (16.5 g) was thus obtained.

Workup

  1. customobtained in the 5th step at 70° C.
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layers were washed with saturated saline
  5. dry with materialthe organic layers were dried over anhydrous sodium sulfate
  6. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 1:1)

Sources & evidence

ORD record
ord-0eded11dc8ab497387c53779e59b8ce5
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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