Dichloromethane → HCID 178459830, compound

HRID 1639967Notes

Reaction equation

HRID 1639967 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:25][CH2:24][CH2:23][C:10]3([C:14](=[O:15])[N:13]([C@H:16]4[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]4)[CH2:12][CH2:11]3)[CH2:9]2)=[CH:4][CH:3]=1.Cl[C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28].C(N(CC)CC)C.C(Cl)Cl>>[OH:22][C@H:19]1[CH2:18][CH2:17][C@H:16]([N:13]2[CH2:12][CH2:11][C:10]3([CH2:23][CH2:24][CH2:25][N:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:27](=[O:28])[O:29][CH:30]([CH3:32])[CH3:31])=[CH:3][CH:4]=4)[CH2:9]3)[C:14]2=[O:15])[CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 178507692HCID 178507692, compound

Product 1

HCID 178459830HCID 178459830, compoundYield 67.5%

Procedure

A mixture of 7-(4-aminophenyl)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (20 mg, 0.00006 mol), isopropyl chloroformate (11 mg, 0.000087 mol), and triethylamine (20 μL, 0.0002 mol) in methylene chloride (300 μL, 0.005 mol) was stirred at rt for 2 h. The crude reaction mixture was purified by prep.-HPLC to afford 17.4 mg of the desired product. LC-MS: 430.3 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by prep.-HPLC

Sources & evidence

ORD record
ord-ced580c7c5344d619d0b2b37f57ac1c6
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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