Cyclohexyl isocyanate → HCID 58770800, compound

HRID 657222Notes

Reaction equation

HRID 657222 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[N:21]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[C:22]=[O:23]>CN(C=O)C>[CH:24]1([NH:21][C:22]([N:18]2[CH2:19][CH2:20][CH:15]([C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH2:16][CH2:17]2)=[O:23])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 595517346,7-Dimethoxy-4-(piperidin-4-yl)quinazoline

Product 1

HCID 58770800HCID 58770800, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6,7-dimethoxy-4-piperidin-4-yl-quinazoline (30 mg, 0.110 mmol), as prepared in Example 1d, in DMF (1 mL) was treated with isocyanato-cyclohexane (20.6 mg, 0.165 mmol) at RT overnight. The reaction was then partitioned between EtOAc (10 mL) and H2O (10 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Purification by prep tlc (1:9 MeOH/DCM) afforded the title compound as a light yellow solid (22 mg, 50%). 1H NMR (300 MHz, CDCl3) δ 9.08 (s, 1H), 7.38 (s, 1H), 7.26 (s, 1H), 4.35 (d, 1H), 4.14 (d, 1H), 4.07 (s, 6H), 3.68 (m, 1H), 3.53 (m, 1H), 3.03 (m, 2H), 2.12-1.90 (m, 4H), 1.70-1.55 (m, 5H), 1.40-1.09 (m, 5H); LC/MS (ESI): calcd mass 398.2, found 399.3 [M+1]+.

Workup

  1. customThe reaction was then partitioned between EtOAc (10 mL) and H2O (10 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by prep tlc (1:9 MeOH/DCM)

Sources & evidence

ORD record
ord-df9e1bdd33ca41a9bc54bfbbc0d75290
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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