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Azetidine → (R)-tert-butyl 1-(3-(azetidine-1-carboxamido)-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

HRID 1923959
Notes
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Reaction equation

HRID 1923959 reaction equation
N1(C(N2C=CN=C2)=O)C=CN=C1.NC1C2C(=NC=C(Br)C=2N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)NC=1.N1CCC1.[Br:42][C:43]1[C:44]([N:60]2[CH2:65][CH2:64][CH2:63][C@@H:62]([NH:66][C:67](=[O:73])[O:68][C:69]([CH3:72])([CH3:71])[CH3:70])[CH2:61]2)=[C:45]2[C:51]([NH:52][C:53]([N:55]3[CH:59]=[CH:58]N=[CH:56]3)=[O:54])=[CH:50][NH:49][C:46]2=[N:47][CH:48]=1>C1COCC1>[N:55]1([C:53]([NH:52][C:51]2[C:45]3[C:46](=[N:47][CH:48]=[C:43]([Br:42])[C:44]=3[N:60]3[CH2:65][CH2:64][CH2:63][C@@H:62]([NH:66][C:67](=[O:73])[O:68][C:69]([CH3:71])([CH3:70])[CH3:72])[CH2:61]3)[NH:49][CH:50]=2)=[O:54])[CH2:59][CH2:58][CH2:56]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10422AzetidineHCID 682631,1'-CarbonyldiimidazoleHCID 67045407(R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamateHCID 67045556(R)-tert-butyl 1-(5-bromo-3-(1H-imidazole-1-carboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

Product 1

HCID 67045546
(R)-tert-butyl 1-(3-(azetidine-1-carboxamido)-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate
Yield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Di(1H-imidazol-1-yl)methanone (3.2 g, 19 mmol) was added to (R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (2.0 g, 4.9 mmol; Example 98, Step A) in THF (100 mL), and the reaction mixture was stirred at room temperature for 18 hours. The reaction solution was used as is. Azetidine (113 mg, 1.98 mmol) was added to (R)-tert-butyl 1-(5-bromo-3-(1H-imidazole-1-carboxamido)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (200 mg, 0.397 mmol) in THF (20 mL), and the reaction was stirred for 18 hours. The reaction was concentrated to dryness and then purified by reverse phase chromatography (SP4, 25M, water/ACN 90/10->0/100, 30 CV) to yield (R)-tert-butyl 1-(3-(azetidine-1-carboxamido)-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (90 mg, 46.0% yield) as a solid.

Workup

  1. stirringthe reaction was stirred for 18 hours
  2. concentrationThe reaction was concentrated to dryness
  3. custompurified by reverse phase chromatography (SP4, 25M, water/ACN 90/10->0/100, 30 CV)

Sources & evidence

ORD record
ord-d91a39833e5540e1bb2314e03bb1a836
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178131B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes