2,4-Dichloro-6-piperidinoquinazoline → HCID 178478384, compound

HRID 855644Notes

Reaction equation

HRID 855644 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:8]=2)[N:3]=1.[CH:19]1([C:22]2[CH:23]=[C:24]([NH2:27])[NH:25][N:26]=2)[CH2:21][CH2:20]1>C(O)C>[Cl:1][C:2]1[N:11]=[C:10]([NH:27][C:24]2[NH:25][N:26]=[C:22]([CH:19]3[CH2:21][CH2:20]3)[CH:23]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 134217992,4-Dichloro-6-piperidinoquinazolineHCID 178507266HCID 178507266, compound

Product 1

HCID 178478384HCID 178478384, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2,4-Dichloro-6-piperidin-1-yl-quinazoline (100 mg, 0.365 mmol), in ethanol (5 omL) was added 5-Cyclopropyl-2H-pyrazol-3-ylamine (88 mg 0.71 mmol). The additional resulted in the formation of a white precipitate. The partial solution was stirred for 10 hr and (2-Chloro-6-piperidin-1-yl-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine was colleted by filtration to give 80 mg (61% yield). HPLC tr=4.90 min (100%), LCMS m/e 369.31 (M+H), 367.28 (M−H) tr=3.41 min, HNMR (500 MHz, dmso): □12.30–12.25 (1H, bs), 10.67 (1H, s), 7.80–7.85 (1H, s), 7.65 91H, d), 7.50 (1H, d), 6.50 (1H, bs), 3.40 (4H, m0, 2.90 (1H, m), 1.70–1.55 (6H, m), 0.95 (2H, m), 0.70 (2H, m).

Workup

  1. customThe additional resulted in the formation of a white precipitate
  2. filtration(2-Chloro-6-piperidin-1-yl-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine was colleted by filtration
  3. customto give 80 mg (61% yield)
  4. customHPLC tr=4.90 min (100%), LCMS m/e 369.31 (M+H), 367.28 (M−H) tr=3.41 min, HNMR

Sources & evidence

ORD record
ord-af407dcdaae64f1eb122732363d8210a
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

Loading…