Dichloromethane → HCID 86590993, compound

HRID 1743734Notes

Reaction equation

HRID 1743734 reaction equation
[NH2:1][C@@H:2]([CH2:13][N:14]1[CH:19]2[CH2:20][CH2:21][CH:15]1[CH2:16][N:17]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18]2)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.C(Cl)Cl.C(N(CC)CC)C.[CH3:39][O:40][C:41](Cl)=[O:42]>O>[CH2:22]([N:17]1[CH2:18][CH:19]2[N:14]([CH2:13][C@H:2]([NH:1][C:41](=[O:42])[O:40][CH3:39])[CH2:3][O:4][C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=3)[CH:15]([CH2:21][CH2:20]2)[CH2:16]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 69622378HCID 69622378, compound

Product 1

HCID 86590993HCID 86590993, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-{[(2S)-2-Amino-3-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]oxy}benzonitrile (3.7 g, 9.8 mmol; from step (f) above) was mixed with DCM (50 mL) and triethylamine (2.1 g, 21.5 mmol). The mixture was cooled to 0° C. and methylchloroformate (0.8 mL, 10.7 mmol) was added dropwise. The reaction was performed under an argon atmosphere. After 2 h, the temperature was allowed to reach r.t, at which temperature it was then stirred overnight. Water was added, the organic layer was separated, dried and evaporated. Purification by chromatography (CHCl3:MeOH (95:5)) gave 2.9 g (68%) of the sub-title compound.

Workup

  1. customthe organic layer was separated
  2. customdried
  3. customevaporated
  4. customPurification by chromatography (CHCl3:MeOH (95:5))

Sources & evidence

ORD record
ord-c86a12e487794f54969267b458bf640f
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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