Cyclopentyl Isocyanate → HCID 86703942, compound

HRID 1049945Notes

Reaction equation

HRID 1049945 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][N:12]=[C:11]3[NH2:18])[CH:5]=[CH:6][CH:7]=1.[N:19]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[C:20]=[O:21]>CN(C)C=O>[NH2:18][C:11]1[C:10]2[C:15](=[CH:16][CH:17]=[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:20]([NH:19][CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:21])[CH:7]=[CH:6][CH:5]=3)[CH:9]=2)[N:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 643500Cyclopentyl IsocyanateHCID 69463478HCID 69463478, compound

Product 1

HCID 86703942HCID 86703942, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 4 mL screw-cap vial was added 6-(3-aminophenyl)quinazolin-4-amine (35 mg; 0.15 mmol) followed by dimethylformamide (0.5 mL) and isocyanatocyclopentane (1.1 equiv., 0.16 mmol, 18 mg). The reaction was stirred at room temperature overnight. The following morning the crude reaction mix was directly purified by reverse phase HPLC, yielding 19 mg of desired product. 1H NMR (400 MHz, DMSO) δ 8.51-8.45 (d, J=1.8 Hz, 1H), 8.45-8.40 (s, 1H), 8.40-8.37 (s, 1H), 8.03-7.95 (dd, J=8.7, 1.9 Hz, 1H), 7.95-7.76 (s, 2H), 7.76-7.70 (d, J=8.7 Hz, 1H), 7.43-7.28 (m, 3H), 6.33-6.20 (d, J=7.2 Hz, 1H), 4.04-3.90 (dd, J=13.4, 6.7 Hz, 1H), 1.93-1.80 (m, 2H), 1.74-1.46 (m, 4H), 1.46-1.32 (m, 2H). LCMS M/Z (M+H)=348.

Workup

  1. customTo a 4 mL screw-cap vial
  2. customThe following morning the crude reaction
  3. additionmix
  4. customwas directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-93d6950b5ddd44c28d57b80d5039a79c
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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