1,2-Dichloroethane → HCID 86629601, compound

HRID 911353Notes

Reaction equation

HRID 911353 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:24][CH2:25][CH2:26][NH: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[NH:27][CH2:26][CH2:25][NH:24][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 938Nicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 57656463HCID 57656463, compound

Product 1

HCID 86629601HCID 86629601, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dissolve nicotinic acid (28.2 mg, 0.23 mmol) in DCM (3 mL). Add EDC (40 mg, 0.208 mmol), HOBT (28.1 mg, 0.2081 mmol) and stir at ambient temperature for 10 min. Add 6-(2-amino-ethylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (70 mg, 0.208 mmol) and stir at ambient temperature for 10 hr. Dilute with DCM, add water and extract the aqueous layer three times with DCM. Wash combined organic extracts with 1N aqueous NaOH, and brine. Dry the organic layer over MgSO4, concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 1:1, 3:7 and 1:9) to obtain 7-chloro-6-{2-[(pyridine-3-carbonyl)-amino]-ethylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine.

Workup

  1. extractionextract the aqueous layer three times with DCM
  2. washWash
  3. dry with materialDry the organic layer over MgSO4
  4. concentrationconcentrate in vacuo
  5. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 1:1, 3:7 and 1:9)

Sources & evidence

ORD record
ord-d184535bc6fc4482b8b19dec780df112
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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