Water → HCID 66785167, compound

HRID 1096628Notes

Reaction equation

HRID 1096628 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].[C:16]([N:23]1[CH2:31][CH2:30][CH2:29][C@@H:25]([C:26](O)=[O:27])[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:26]([C@@H:25]2[CH2:29][CH2:30][CH2:31][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24]2)=[O:27])=[C:3]([NH:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66785441HCID 66785441, compound

Product 1

HCID 66785167HCID 66785167, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-3-(3-methoxypropylamino)benzonitrile (41B) (3.50 mmol, 718 mg) in DMF (25 mL) was added (R)-(−)—N-Boc-Nipecotic acid (4.55 mmol, 1.04 g) and N-methylmotpholine (10.50 mmol, 1.15 mL). The reaction mixture was stirred at rt for 5 min and then added HATU (5.25 mmol, 2.00 g) and kept stirring at rt overnight. The reaction mixture was poured into H2O, extracted with EtOAc. The extract was washed with H2O, NaHCO3, brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel EtOAc-hexane: 1:2) to afford (R)-tert-butyl 3-(4-cyano-2-(3-methoxypropylamino)phenylcarbamoyl)piperidine-1-carboxylate (41C) (2.40 mmol, 1.01 g, three-step yield: 68.6%). ESI-MS: m/z 417.5 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with H2O, NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by flash chromatography (silica gel EtOAc-hexane: 1:2)

Sources & evidence

ORD record
ord-38b0880e009a4babbc6dc914dba65e5e
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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