4-Methylmorpholine → HCID 58548177, compound

HRID 467725

Reaction equation

HRID 467725 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].[CH:8]1([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[CH:28]=[N:27][CH:26]=[CH:25][C:21]=3[C:22](O)=[O:23])=[O:18])[C:14]([NH:29][C:30]3[CH:31]=[N:32][CH:33]=[N:34][CH:35]=3)=[N:13][CH:12]=2)[CH2:10][CH2:9]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:22]([C:21]1[CH:25]=[CH:26][N:27]=[CH:28][C:20]=1[NH:19][C:17]([C:15]1[C:14]([NH:29][C:30]2[CH:35]=[N:34][CH:33]=[N:32][CH:31]=2)=[N:13][CH:12]=[C:11]([CH:8]2[CH2:10][CH2:9]2)[N:16]=1)=[O:18])=[O:23])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 5338662-(Propan-2-yloxy)ethan-1-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 700989283-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-isonicotinic acid

Product 1

HCID 58548177HCID 58548177, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-aminoethyl isopropyl ether (25 mg, 242 μmol) and 3-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-isonicotinic acid (101 mg, 267 μmol) at rt in THF (5 ml) under an argon atmosphere were added 4-methylmorpholine (123 mg, 134 μl, 1.21 mmol) and HATU (184 mg, 485 μmol). The mixture was heated to reflux and stirring was continued for 1 day. The reaction mixture was concentrated. The crude product was purified by silica gel chromatography using an EtOAc/MeOH gradient as eluent. After trituration with MeOH, the title compound (90 mg, 80%) was obtained as yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b4c10af434614ecbaae0174a684336ff
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Linked notes

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