4-Methylmorpholine → HCID 74222626, compound

HRID 1844224Notes

Reaction equation

HRID 1844224 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:13]([C:17](O)=[O:18])=[C:14]([CH3:16])[N:15]=2)[CH:9]=[CH:10][C:11]=1[F:12].F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:54][C@H:55]([CH2:58][CH2:59][CH2:60][CH3:61])[CH2:56][OH:57]>CN(C=O)C>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:13]([C:17]([NH:54][C@H:55]([CH2:58][CH2:59][CH2:60][CH3:61])[CH2:56][OH:57])=[O:18])=[C:14]([CH3:16])[N:15]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

7

Reactant 5

HCID 79724-Methylmorpholine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6994402(R)-2-Aminohexan-1-ol2×HCID 86717941HCID 86717941, compoundHCID 178484679HCID 178484679, compound

Product 1

HCID 74222626HCID 74222626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 mg (0.04 mmol) of 8-[(2,6-difluorobenzyl)oxy]-7-fluoro-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 112A, 20 mg (0.06 mmol) of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate (TBTU) and 17 mg (0.17 mmol) of 4-methylmorpholine were initially charged in 0.28 ml of DMF. 7.5 mg (0.06 mmol) of (2R)-2-aminohexan-1-ol were then added, and the mixture was stirred at RT overnight. Another 2.6 mg of TBTU, 4 mg of 4-methylmorpholine and 1 mg of (2R)-2-aminohexan-1-ol were added, and the mixture was stirred at RT for 2 h. The reaction mixture was concentrated and purified by thick-layer chromatography (mobile phase: dichloromethane/methanol=10/1). This gave 12 mg (66% of theory; purity 99%) of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by thick-layer chromatography (mobile phase: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-62580a090fbf435e8140cc119cd570d6
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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