3,4-Dichlorophenyl isocyanate → HCID 59149873, compound

HRID 655561Notes

Reaction equation

HRID 655561 reaction equation
Cl.Cl.[OH:3][C@@H:4]1[CH2:11][N:10]([CH2:12][CH2:13][CH2:14][N:15]2[C:21](=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:9][CH2:8][C:5]21[CH2:7][CH2:6]2.[Cl:23][C:24]1[CH:25]=[C:26]([N:31]=[C:32]=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]>>[Cl:23][C:24]1[CH:25]=[C:26]([NH:31][C:32]([N:18]2[CH2:19][CH2:20][C:21](=[O:22])[N:15]([CH2:14][CH2:13][CH2:12][N:10]3[CH2:9][CH2:8][C:5]4([CH2:6][CH2:7]4)[C@H:4]([OH:3])[CH2:11]3)[CH2:16][CH2:17]2)=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

3

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 86638113HCID 86638113, compound

Product 1

HCID 59149873HCID 59149873, compound

Procedure

In analogy to the procedure described in example 5, 4-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-[1,4]diazepan-5-one dihydrochloride (US 2007249589, described as 4-[3-((−)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-[1,4]diazepan-5-one dihydrochloride) and 3,4-dichlorophenyl isocyanate gave after separation with flash chromatography (silicycle SiO2, dichloromethane/methanol 95:5 to 4:1) 43% of the title compound as white solid. MS: 469.3 (MH+, 2Cl).

Workup

  1. customgave
  2. customafter separation with flash chromatography (silicycle SiO2, dichloromethane/methanol 95:5 to 4:1) 43% of the title compound as white solid

Sources & evidence

ORD record
ord-fa25dce104fc48e996f3a7ab7870678b
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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