p-Toluenesulfonic acid → HCID 59361778, compound

HRID 1968623Notes

Reaction equation

HRID 1968623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[C:25]3[C:24]([NH2:26])=[N:23][CH:22]=[N:21][C:20]=3[NH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[O:58]1CCO[CH:59]1[CH:63]1[CH2:68][CH2:67][CH2:66][CH:65](O)[CH2:64]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[NH2:26][C:24]1[C:25]2[C:17]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=4)=[C:2]([Cl:1])[CH:3]=3)=[CH:18][N:19]([CH:65]3[CH2:66][CH2:67][CH2:68][CH:63]([CH:59]=[O:58])[CH2:64]3)[C:20]=2[N:21]=[CH:22][N:23]=1

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14296102HCID 14296102, compoundHCID 68565736HCID 68565736, compound

Product 1

HCID 59361778HCID 59361778, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3—CHloro-4-(3-fluorobenzyloxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (prepared according to a similar procedure as described in Example 1) (1 equivalent) is placed in THF. Triphenyl phosphine (1.5 equivalents) is added, followed by dropwise addition of DEAD (3 equivalents). 3-(1,3-dioxolan-2-yl)cyclohexanol (1 equivalent) is added and the mixture is stirred at room temperature overnight. The reaction mixture is partitioned between EtOAc and water, the organic layer is separated, washed with water, brine, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and suspended in acetone. p-Toluensulfonic acid (0.6 equivalent) is added and the mixture is refluxed for 4 h. The mixture is filtered, the filtrate is concentrated in vacuo and purified by column chromatography.

Workup

  1. customThe reaction mixture is partitioned between EtOAc and water
  2. customthe organic layer is separated
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. temperaturethe mixture is refluxed for 4 h
  8. filtrationThe mixture is filtered
  9. concentrationthe filtrate is concentrated in vacuo
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-03a7093b451946928dc0de39b67334c5
Source dataset
uspto-grants-2013_04
Patent number
US08426428B2

Reaction notes

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