Diisopropylethylamine → 1-(2-Chloro-4-cyano-phenyl)-3-(2-hydroxymethyl-indan-2-yl)-urea

HRID 1092344Notes

Reaction equation

HRID 1092344 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)C(C)C)(C)C.Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:32][C:33]1([CH2:42][OH:43])[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34]1>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]([NH:32][C:33]1([CH2:42][OH:43])[CH2:34][C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:41]1)=[O:23]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 5198964-Amino-3-chlorobenzonitrileHCID 22080542(2-Amino-2,3-dihydro-1H-inden-2-yl)methanol

Product 1

HCID 574956291-(2-Chloro-4-cyano-phenyl)-3-(2-hydroxymethyl-indan-2-yl)-ureaYield 244.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-chloro-4-cyano-aniline (150 mg) and N,N-diisopropylethylamine (0.34 ml) in THF (15 ml), a solution of triphosgene (96 mg) in THF (5 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for 30 min. To the mixture, a solution of 2-amino-2,3-dihydro-1H-indene-2-methanol (160 mg, WO 9110644) in THF (2 ml) was added at room temperature. The mixture was stirred for 1 hr at room temperature. The mixture was diluted with AcOEt, washed with water and brine, dried over MgSO4 and evaporated. The residue was triturated with CH2Cl2 to obtain the title compound (270 mg, 80%) as a white solid.

Workup

  1. stirringThe mixture was stirred for 1 hr at room temperature
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-985ae49f82b940a6a0f6680c06c74bd4
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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