Isopropyl isocyanate → HCID 86583549, compound

HRID 1066614Notes

Reaction equation

HRID 1066614 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][C:9]=1[CH2:29][CH3:30]>C1COCC1>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([NH:20][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])=[C:9]([CH2:29][CH3:30])[CH:10]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:26][CH:25]=1)#[N:28]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanate2×HCID 86583550HCID 86583550, compound

Product 1

HCID 86583549HCID 86583549, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of isopropyl isocyanate (130 mg, 1.55 mmol) in THF (2 ml) was added to a solution of the ethyl (RS)-(4-amino-3-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (500 mg, 1.55 mmol) described in Example 186.1 in THF (10 ml). The mixture was stirred overnight at room temperature. Thereafter, further isopropyl isocyanate (260 mg, 3.1 mmol) was added and the mixture was stirred overnight at 50° C. The reaction mixture was concentrated. The residue was suspended in CH2Cl2/MeOH (98:2) and the colorless solid was filtered off. The solid was washed with EtOH and dried under a high vacuum. Ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-4-(3-isopropylureido)-phenyl]-acetate (395 mg, 62%) was obtained as a colorless solid; MS: 409 ([M+H]+)

Workup

  1. stirringthe mixture was stirred overnight at 50° C
  2. concentrationThe reaction mixture was concentrated
  3. filtrationthe colorless solid was filtered off
  4. washThe solid was washed with EtOH
  5. customdried under a high vacuum

Sources & evidence

ORD record
ord-4a2666c6d64d44e99553ffa858b370b7
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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