4-Methylmorpholine → HCID 11247409, compound

HRID 2075471Notes

Reaction equation

HRID 2075471 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](/[CH:24]=[CH:25]/[C:26]2[CH:39]=[CH:38][C:29]([C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:31])=[CH:28][CH:27]=2)=[N:16]1.C(OC([N:47]1[CH2:54][CH2:53][CH2:52][C@H:48]1[C:49](O)=[O:50])=O)(C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.Cl.CO>CO>[NH:47]1[CH2:54][CH2:53][CH2:52][C@H:48]1[C:49]([N:35]1[CH2:36][CH2:37][N:32]([C:30](=[O:31])[C:29]2[CH:28]=[CH:27][C:26](/[CH:25]=[CH:24]/[C:17]3[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[NH:15][N:16]=3)=[CH:39][CH:38]=2)[CH2:33][CH2:34]1)=[O:50]

Participants

9

Reactant 7

HCID 79724-MethylmorpholineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanoneHCID 21893726Hydrochloride methanol

Product 1

HCID 11247409HCID 11247409, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product obtained using dihydrochloride of Compound 18 (100 mg, 0.25 mmol), N-(tert-butoxycarbonyl)-L-proline (53 mg, 0.25 mmol), 1-hydroxybenzotriazole monohydrate (43 mg, 0.33 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (66 mg, 0.35 mmol) and N-methylmorpholine (0.06 mL, 0.50 mmol) in a similar manner to Example 5, was dissolved in methanol (2.00 mL), and the solution was added with 4 mol/L hydrogen chloride-methanol solution (1.50 mL) followed by heating under reflux at 60° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was added with saturated sodium hydrogencarbonate solution and ethyl acetate, followed by extraction. The crude product was crystallized from acetone to obtain Compound 140 (21 mg, 20%).

Workup

  1. customThe product obtained
  2. temperatureby heating
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was added with saturated sodium hydrogencarbonate solution and ethyl acetate
  5. extractionfollowed by extraction
  6. customThe crude product was crystallized from acetone

Sources & evidence

ORD record
ord-3fbce1c0c4404f2da8f026c5218c40ad
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

Loading…