Dimethylamine → HCID 66701311, compound

HRID 876339Notes

Reaction equation

HRID 876339 reaction equation
[C:1]1([C:7]([NH:9][CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:26]([N:28]3[CH2:33][CH2:32][CH:31]([C:34](O)=[O:35])[CH2:30][CH2:29]3)=[O:27])[CH2:11]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:37][N:38](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:39].F[P-](F)(F)(F)(F)F.CNC>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:37][N:38]([CH3:39])[C:34]([CH:31]1[CH2:30][CH2:29][N:28]([C:26]([N:12]2[CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=3)[CH2:15][CH:10]([NH:9][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:8])[CH2:11]2)=[O:27])[CH2:33][CH2:32]1)=[O:35]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 46931521HCID 46931521, compound

Product 1

HCID 66701311HCID 66701311, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

85 mg (0.17 mmol) of 1-({3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}carbonyl)piperidine-4-carboxylic acid together with 80 mg (0.21 mmol) of HATU and 34 mg (0.28 mmol) of 4-dimethylaminopyridine were initially charged in 1.3 ml of DMF, and 6 mg (0.14 mmol) of N-methylmethanamine were added. The reaction mixture was stirred overnight at RT and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 62 mg (69% of theory)

Workup

  1. custompurified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-1682679a2f5046f0b070be3af3becdf9
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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