Morpholine → HCID 86597640, compound

HRID 751600Notes

Reaction equation

HRID 751600 reaction equation
C([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:18]3[N:19]=[C:20]([NH:27][C:28]4[CH:36]=[CH:35][C:31]([C:32]([OH:34])=O)=[CH:30][CH:29]=4)[C:21]4[N:22]([CH:24]=[CH:25][N:26]=4)[CH:23]=3)[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)(C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=[CH:52][CH:53]=[CH:54][C:49]=2N=N1.[NH:66]1[CH2:71][CH2:70][O:69][CH2:68][CH2:67]1>O>[CH2:49]([C:7]1[CH:6]=[CH:5][CH:38]=[CH:37][C:8]=1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[N:19]=[C:20]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([C:32]([N:66]4[CH2:71][CH2:70][O:69][CH2:68][CH2:67]4)=[O:34])=[CH:35][CH:36]=3)[C:21]3[N:22]([CH:24]=[CH:25][N:26]=3)[CH:23]=2)[CH:13]=1)=[O:10])[CH2:54][CH2:53][CH3:52]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11663420HCID 11663420, compound

Product 1

HCID 86597640HCID 86597640, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-{6-[3-(4-tert-butyl-benzoylamino)phenyl]imidazo[1,2-a]pyrazin-8-ylamino}benzoic acid (21) (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. Morpholine (0.48 mmol) is added and the mixture is stirred at room temperature or 16 hrs. Water (10 mL) is added and the mixture extracted with ethyl acetate (2×70 mL), the extracts are washed with water (2×30 mL) and brine (1×30 mL), dried over magnesium sulfate, and concentrated in vacuo. The residue is triturated with diethyl ether to give 4-tert-B\butyl-N-(3-{8-[4-(morpholine-4-carbonyl)-phenylamino]imidazo[1,2-a]pyrazin-6-yl}-phenyl)benzamide (22) as a cream solid.

Workup

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

Sources & evidence

ORD record
ord-a86c6e305edd4aeab1669be3761e3815
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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