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Acetic Acid → 6-(3-hydroxyphenyl)-4-(1H-indazol-5-ylamino)-2-morpholin-4-ylpyrimidine-5-carboxylic acid

HRID 30440
Notes
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Reaction equation

HRID 30440 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12](C3C=CNN=3)[N:11]=[C:10]([NH:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][N:24]=[CH:23]4)[C:9]=2[C:29]([OH:31])=[O:30])[CH:5]=[CH:6][CH:7]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(O)(=O)C>CN1C(=O)CCC1>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:11]=[C:10]([NH:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][N:24]=[CH:23]4)[C:9]=2[C:29]([OH:31])=[O:30])[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 178524705HCID 178524705, compound

Product 1

HCID 597897286-(3-hydroxyphenyl)-4-(1H-indazol-5-ylamino)-2-morpholin-4-ylpyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

Resin bound 6-(3-hydroxyphenyl)-4-(1H-indazol-5-ylamino)-2-pyrazolylpyrimidine-5-carboxylic acid (100 mg, 0.055 mmol, 1 eq) was suspended in NMP, and morpholine (144 μL, 144 mg, 1.65 mmol, 30 eq) was added, followed by acetic acid (31 μL, 33 mg, 0.55 mmol, 10 eq). The reaction mixture was shaken at 90° C. overnight. The resin was filtered and washed with DMF, water, MeOH, CH2Cl2, then dried. The resin was treated with 95% TFA/H2O for 1.5 h at room temperature. Filtration and evaporation under reduced pressure afforded 6-(3-hydroxyphenyl)-4-(1H-indazol-5-ylamino)-2-morpholin-4-ylpyrimidine-5-carboxylic acid.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with DMF, water, MeOH, CH2Cl2
  3. customdried
  4. additionThe resin was treated with 95% TFA/H2O for 1.5 h at room temperature
  5. filtrationFiltration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-b0d78c60a3bd4575a1579652b65318a0
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423148B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes