Morpholine → [4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanone

HRID 751587Notes

Reaction equation

HRID 751587 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>O>[Br:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)=[O:18])=[CH:19][CH:20]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 597546904-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic Acid

Product 1

HCID 59754722[4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid (7) (0.16 mmol), benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (0.16 mmol), and N′N-diisopropylethylamine (0.48 mmol) is stirred at room temperature for 20 min. under N2. Morpholine (0.48 mmol) is added and the mixture is stirred at room temperature for 16 hr. Water (10 mL) is added and the mixture extracted with ethyl acetate (2×70 mL). The extracts are subsequently washed with water (2×30 mL) and brine (1×30 mL), dried over sodium sulfate, and concentrated in vacuo. The residue is triturated with diethyl ether to give [4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanone (8) as a cream solid.

Workup

  1. stirringthe mixture is stirred at room temperature for 16 hr
  2. extractionthe mixture extracted with ethyl acetate (2×70 mL)
  3. washThe extracts are subsequently washed with water (2×30 mL) and brine (1×30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-097e6b8ff7e3407baaa5592c51594d9f
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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