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1,2-Dichloroethane → HCID 86629597, compound

HRID 2041118
Notes
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Reaction equation

HRID 2041118 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:24][CH2:25][CH2:26][O:27][C:28]1[C:38]2[CH2:37][CH2:36][N:35]([C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])[CH2:34][CH2:33][C:32]=2[CH:31]=[CH:30][C:29]=1[Cl:45]>C(Cl)Cl.O>[Cl:45][C:29]1[CH:30]=[CH:31][C:32]2[CH2:33][CH2:34][N:35]([C:39](=[O:44])[C:40]([F:42])([F:41])[F:43])[CH2:36][CH2:37][C:38]=2[C:28]=1[O:27][CH2:26][CH2:25][NH:24][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 57655967HCID 57655967, compound

Product 1

HCID 86629597HCID 86629597, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

Combine picolinic acid (40 mg, 0.327 mmol), EDC (57 mg, 0.297 mmol) and HOBT (40 mg, 0.297 mmol) in DCM (3 mL). Stir for 10 min at ambient temperature. Add 6-(2-amino-ethoxy)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (100 mg, 0.297 mmol). Stir for 16 h at ambient temperature. Dilute with DCM, add water and extract the aqueous layer with DCM. Wash the combined organic extracts with 1M aqueous NaOH and brine. Dry the organic layer over MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (3:2) to give 7-chloro-6-{2-[(pyridine-2-carbonyl)-amino]-ethoxy}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (94 mg, 74%).

Workup

  1. stirringStir for 16 h at ambient temperature
  2. extractionextract the aqueous layer with DCM
  3. washWash the combined organic extracts with 1M aqueous NaOH and brine
  4. dry with materialDry the organic layer over MgSO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-5d21c45e86b549cab862e89f17888d70
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580780B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes