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Diisopropylethylamine → HCID 86726715, compound

HRID 1499481
Notes
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Reaction equation

HRID 1499481 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:14]=[CH:15][C:3]=12.[NH:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]1.CCN(C(C)C)C(C)C>C(O)CCC>[C:34]([O:33][C:32]([NH:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[N:14]=[CH:15][C:3]=23)[CH2:26]1)=[O:38])([CH3:37])([CH3:35])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 53665897Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 86726715HCID 86726715, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 2631-Butanol
Solvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.5 g, 4.3 mmol), tert-butyl (3S)-piperidin-3-ylcarbamate (1.0 g, 5.0 mmol) and DIPEA (0.84 g, 6.5 mmol) in 1-butanol (10 mL) was heated to 140° C. for 14 h, then allowed to cool. The mixture was concentrated under reduced pressure, and the resulting residue was diluted with EtOAc and washed with aq. NaHCO3. The organic extract was washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash® apparatus, eluting with 20-100% EtOAc in hexanes, to give the sub-title compound (1.9 g, 86%). LCMS calc. for C27H36N5O5 (M+H)+: m/z=510.3. Found: 510.2.

Workup

  1. temperatureto cool
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe resulting residue was diluted with EtOAc
  4. washwashed with aq. NaHCO3
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel using CombiFlash® apparatus
  10. washeluting with 20-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-d6440e608d5f402f9e0181610cd447ee
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09200004B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes