4-Methylmorpholine → HCID 74222628, compound

HRID 1624142Notes

Reaction equation

HRID 1624142 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[OH:11].[CH3:12][C:13]1[N:14]=[C:15]2[C:20]([O:21][CH2:22][CH2:23][CH:24]([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:19][C:18]([CH3:33])=[CH:17][N:16]2[C:34]=1[C:35](O)=[O:36].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[OH:11][CH:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]1[NH:1][C:35]([C:34]1[N:16]2[CH:17]=[C:18]([CH3:33])[CH:19]=[C:20]([O:21][CH2:22][CH2:23][CH:24]([C:25]([F:28])([F:27])[F:26])[C:29]([F:30])([F:31])[F:32])[C:15]2=[N:14][C:13]=1[CH3:12])=[O:36]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 1390341-Amino-2-indanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867179342,6-Dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 74222628HCID 74222628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12 mg (0.08 mmol) of 1-aminoindan-2-ol were initially charged, 31 mg (0.08 mmol) of 2,6-dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylic acid Example 91A, dissolved in 0.3 ml of DMF, 40 mg (0.104 mmol) of HATU, dissolved in 0.3 ml of DMF, and then 16 mg (0.16 mmol) of 4-methylmorpholine were added and the mixture was shaked at RT overnight. The target compound was isolated by preparative HPLC (Method 11). This gave 15 mg (36% of theory).

Workup

  1. customThe target compound was isolated by preparative HPLC (Method 11)

Sources & evidence

ORD record
ord-64a87e6dbc1540998479225760144903
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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