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Azepane → HCID 59553057, compound

HRID 1943615
Notes
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Reaction equation

HRID 1943615 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([N:19]2[C:27]3[CH2:26][CH2:25][CH2:24][CH:23]([CH2:28][C:29]([OH:31])=O)[C:22]=3[CH:21]=[N:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:32]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[C:13]1([N:19]2[C:27]3[CH2:26][CH2:25][CH2:24][CH:23]([CH2:28][C:29]([N:32]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:31])[C:22]=3[CH:21]=[N:20]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8119AzepaneHCID 682631,1'-CarbonyldiimidazoleHCID 59553060HCID 59553060, compound

Product 1

HCID 59553057HCID 59553057, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

CDI (63.2 mg, 0.39 mmol) is added to a solution of 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetic acid (100 mg, 0.39 mmol) in CH2Cl2 (20 mL) cooled in an ice bath, and is heated to 45° C. for 2.5 hours. Then it is cooled to 0° C. and azacycloheptane (38.7 mg, 0.39 mmol) is added and is heated at 45° C. for 1 hour. The solvent is evaporated under reduced pressure, diluted in AcOEt and washed with diluted HCl. The organic phase is dried and evaporated under reduced pressure. The resulting crude product is purified by means of silica gel chromatography, giving 1-(2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetyl)azepane (45 mg, 0.13 mmol, 33%, oil).

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThen it is cooled to 0° C.
  3. temperatureis heated at 45° C. for 1 hour
  4. customThe solvent is evaporated under reduced pressure
  5. additiondiluted in AcOEt
  6. washwashed with diluted HCl
  7. customThe organic phase is dried
  8. customevaporated under reduced pressure
  9. customThe resulting crude product is purified by means of silica gel chromatography

Sources & evidence

ORD record
ord-cb327f08a4f5486dbd3e1a60a0cdf20c
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394797B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes