Ethyl Acetate → HCID 178430154, compound

HRID 2168233Notes

Reaction equation

HRID 2168233 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.CCOC(C)=O>CN1C(=O)CCC1>[CH3:11][C:10]1[C:3]2[C:4]([NH:5][CH:6]=[N:7][C:2]=2[N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 118120N-4-PiperidylbenzamideHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 178430154HCID 178430154, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine D4 (136 mg), N-4-piperidinylbenzamide (249 mg, 1.217 mmol) and DIPEA (0.354 mL, 2.029 mmol) in NMP (1 mL) was heated in the microwave at 150° C. for 20 minutes. EtOAc (10 mL) was added to the mixture and a precipitate formed which was filtered off—this was shown to be remaining piperidinylbenzamide starting material. The filtrate was diluted with further EtOAc (10 mL) and washed with water (3×15 mL). On the third washing a precipitate formed—this was filtered off and found to be mainly desired product. The filtrate was dried (phase separator) and concentrated to give further solid. Both solids were purified by MDAP and the clean fractions combined and concentrated in vacuo before drying in a drying pistol to give E17 (117 mg); 1H NMR (d6-DMSO) δ 11.54 (1H, brs), 8.48 (1H, d), 8.21 (1H, s), 7.86 (2H, d), 7.52 (1H, t), 7.45 (2H, t), 7.08 (1H, s), 4.13-3.98 (3H, m), 3.04 (2H, t), 2.33 (3H, s), 1.93 (2H, dd), 1.72 (2H, ddd), MS(ES+) 336 [M+H]+.

Workup

  1. customa precipitate formed which
  2. filtrationwas filtered off—this
  3. additionThe filtrate was diluted with further EtOAc (10 mL)
  4. washwashed with water (3×15 mL)
  5. customOn the third washing a precipitate formed—this
  6. filtrationwas filtered off
  7. customThe filtrate was dried (phase separator)
  8. concentrationconcentrated
  9. customto give further solid
  10. customBoth solids were purified by MDAP
  11. concentrationconcentrated in vacuo
  12. custombefore drying in a drying pistol
  13. customto give E17 (117 mg)

Sources & evidence

ORD record
ord-6a43e3ea711a4186992634bd47bc1fc0
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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