Pyridine → HCID 10432375, compound

HRID 2109519Notes

Reaction equation

HRID 2109519 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]=[CH:7]2.N1C=CC=CC=1.Cl[C:20](OC1C=CC=CC=1)=[O:21].C(N(CC)CC)C.[NH2:36][CH:37]1[CH2:40][N:39]([CH:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:38]1>ClCCl>[CH3:12][C:5]1[N:6]=[CH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([NH:1][C:20]([NH:36][CH:37]1[CH2:40][N:39]([CH:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:38]1)=[O:21])[CH:11]=[CH:10][CH:9]=2

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 57445463-Amino-1-(diphenylmethyl)azetidineHCID 122120553-Methylisoquinolin-5-amine

Product 1

HCID 10432375HCID 10432375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

D4 (73 mg, 0.46 mmol) in dry dichloromethane (5 ml) was treated with pyridine (45 ul, 0.55 mmol) followed by phenyl chloroformate (69 ul, 0.55 mmol). After 1 h triethylamine (128 ul, 0.92 mmol) was added, followed by D16 (0.46 mmol). The reaction mixture was then stirred overnight at ambient temperature. The precipitate was separated by centrifugation, washed with DCM, diethyl ether and then dried to give the title compound as a yellow solid. MH+ 423.

Workup

  1. customThe precipitate was separated by centrifugation
  2. washwashed with DCM, diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-993fe47287f04759ad1c56c431fbe22e
Source dataset
uspto-grants-2009_04
Patent number
US07514562B2

Reaction notes

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