Phenyl isocyanate → HCID 69458742, compound

HRID 971069Notes

Reaction equation

HRID 971069 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH2:17])[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN1CCOCC1>C1(C)C=CC=CC=1>[NH2:17][C:10]1[C:11]2[N:12]([CH:14]=[CH:15][N:16]=2)[CH:13]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25]([NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:26])=[CH:7][CH:6]=2)[N:9]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 79724-MethylmorpholineHCID 694567936-(4-Aminophenyl)imidazo[1,2-a]pyrazin-8-amine

Product 1

HCID 69458742HCID 69458742, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(FIG. 1) Procedure: A mixture of 1.00 eq. of 6-(4-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-ylamine, 1.50 eq. of phenylisocyanate, and 2.00 eq. of N-methylmorpholine, in toluene is mixed at room temperature for 2 hr. The mixture is partitioned between 1 N NaOH and ethyl acetate and extracted three times. The organic extracts are combined and dried over MgSO4. The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography (50% ethyl acetate/hexanes) to yield 8.

Workup

  1. customThe mixture is partitioned between 1 N NaOH and ethyl acetate
  2. extractionextracted three times
  3. dry with materialdried over MgSO4
  4. customThe solvent is removed under reduced pressure
  5. customthe resulting residue is purified by flash chromatography (50% ethyl acetate/hexanes)
  6. customto yield 8

Sources & evidence

ORD record
ord-c2e39bade0e94ce7aaae0a8dd2e5cc19
Source dataset
uspto-grants-2007_12
Patent number
US07312341B2

Reaction notes

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