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Diisopropylethylamine → (R)-tert-butyl 3-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate

HRID 1969780
Notes
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Reaction equation

HRID 1969780 reaction equation
CCN(C(C)C)C(C)C.Cl.[S:11]([N:21]1[C:25]2=[N:26][CH:27]=[C:28]([CH2:30][NH2:31])[N:29]=[C:24]2[CH:23]=[CH:22]1)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[C:32]([N:39]1[CH2:44][CH2:43][CH2:42][C@@H:41]([C:45](O)=[O:46])[CH2:40]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[S:11]([N:21]1[C:25]2=[N:26][CH:27]=[C:28]([CH2:30][NH:31][C:45]([C@@H:41]3[CH2:42][CH2:43][CH2:44][N:39]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:40]3)=[O:46])[N:29]=[C:24]2[CH:23]=[CH:22]1)([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=1)(=[O:12])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67068339(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride

Product 1

HCID 58557667
(R)-tert-butyl 3-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate
Yield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

DIEA (7.7 mL, 44.3 mmol) was added to a solution of (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride (5 g, 14.7 mmol) in DCM (78 mL) and the reaction was stirred at ambient temperature for about 10 min followed by the addition of (R)-N-Boc-piperidine-3-carboxylic acid (3.38 g, 14.7 mmol, CNH-Technologies) and HATU (5.61 g, 14.7 mmol). The mixture was stirred for about 1 h, then water (30 mL) was added, and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (30 mL) and brine (30 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to afford crude (R)-tert-butyl 3-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate (7.58 g, 94%): LC/MS (Table 1, Method b) Rt=2.30 min; MS m/z: 514 (M+H)+.

Workup

  1. stirringThe mixture was stirred for about 1 h
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (30 mL) and brine (30 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with a gradient of 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-277e02eed51a4bfbba2406251c5dcf64
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426411B2

Reaction notes

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