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Ethyl Acetate → HCID 59596400, compound

HRID 2264581
Notes
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Reaction equation

HRID 2264581 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([NH:17][C:18]([N:20]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3[CH:27]=[C:28]([OH:31])[CH:29]=[CH:30][C:21]2=3)=[O:19])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1.[NH2:34][C:35]1[N:40]=[C:39](Cl)[CH:38]=[C:37]([Cl:42])[N:36]=1.[OH-].[Na+].CCOC(C)=O>CC(C)=O.O.CN1C(=O)N(C)CC1>[F:33][C:2]([F:32])([F:1])[C:3]1[CH:4]=[C:5]([NH:17][C:18]([N:20]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3[CH:27]=[C:28]([O:31][C:39]4[CH:38]=[C:37]([Cl:42])[N:36]=[C:35]([NH2:34])[N:40]=4)[CH:29]=[CH:30][C:21]2=3)=[O:19])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 86618288HCID 86618288, compound

Product 1

HCID 59596400HCID 59596400, compound

Reagents, catalysts & solvents 3

HCID 180
Acetone
Solvent
HCID 962WaterSolvent2×
HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 300 mg (0.65 mMol) of 7-hydroxy-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid [3-trifluoromethyl-4-(4-methylpiperazin-1-ylmethyl)-phenyl]-amide (Step 12.2), 106 mg (0.65 mMol) 2-amino-4,6-dichloro-pyrimidine and 26 mg (0.65 mMol) NaOH in 2 ml acetone, 2 ml H2O and 1.2 ml DMEU is stirred at 60° C. for 12 h. Then the suspension is dissolved by addition of water and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Reversed phase MPLC (Gilson system) gives the title compound: MS: [M+1]+=590/592; HPLC: AtRet=12.7.

Workup

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9fb9e29aacc54581babd47fdba235641
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07855215B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes