Dichloromethane → HCID 178436271, compound

HRID 644362Notes

Reaction equation

HRID 644362 reaction equation
[NH2:1][C@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([CH2:27][CH3:28])[CH:20]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].C(Cl)Cl.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:44][CH2:43][C:42]3[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=3[NH:40][C:39]2=[O:49])[CH2:34][CH2:33]1>C(#N)C>[CH2:27]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[CH2:25][CH3:26])[CH2:18][C@@H:2]([NH:1]/[C:35](=[N:38]/[C:39]#[N:40])/[N:32]1[CH2:33][CH2:34][CH:35]([N:38]2[CH2:44][CH2:43][C:42]3[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=3[NH:40][C:39]2=[O:49])[CH2:36][CH2:37]1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4])[CH3:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 11560098(R)-2-amino-3-(3,4-diethyl-phenyl)-1-[4-(1-methylpiperidin-4-yl)-piperazin-1-yl]-propan-1-one

Product 1

HCID 178436271HCID 178436271, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 390 mg (1.01 mmol) (R)-2-amino-3-(3,4-diethyl-phenyl)-1-[4-(1-methylpiperidin-4-yl)-piperazin-1-yl]-propan-1-one, 270 mg (1.01 mmol) diphenylcyano-carbonimidate and 50 mL DCM was stirred for 4 h at RT and then evaporated down under reduced pressure. The residue was combined with 30 mL acetonitrile and 270 mg (1.10 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and refluxed for 14 h. The reaction mixture was evaporated down under reduced pressure and the residue was purified by chromatography. The product fractions were evaporated down, the residue was triturated with PE and suction filtered.

Workup

  1. customevaporated down under reduced pressure
  2. temperaturerefluxed for 14 h
  3. customThe reaction mixture was evaporated down under reduced pressure
  4. customthe residue was purified by chromatography
  5. customThe product fractions were evaporated down
  6. customthe residue was triturated with PE and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-8daf2e57f51b436ab7429d60ed8b0c2a
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

Loading…