Morpholine → HCID 24770741, compound

HRID 2221154Notes

Reaction equation

HRID 2221154 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=4)=[N:18][N:17]4[CH2:27][CH2:28][CH2:29][C:16]=34)[CH:11]=2)[N:6]=[CH:5]1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[CH3:26][C:22]1[N:21]=[C:20]([C:19]2[C:15]([C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][CH:9]=3)[N:6]=[CH:5][N:4]([CH2:3][CH2:2][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:13]4=[O:14])=[C:16]3[CH2:29][CH2:28][CH2:27][N:17]3[N:18]=2)[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 11502346HCID 11502346, compound

Product 1

HCID 24770741HCID 24770741, compoundYield 74%

Conditions

Temperature
140 °C

Procedure

Combine 3-(2-chloro-ethyl)-6-[2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-3H-quinazolin-4-one (Example 6; 30 mg, 0.07 mmol) and morpholine (1 mL) in a pressure tube. Seal the tube and place in a microwave reactor. Radiate the mixture and heat at 140° C. for 1 h. The crude product is purified with silica gel chromatography, using dichloromethane to 10:1 dichloromethane/methanol as eluting solvents to give 25 mg (74%) of the target compound. MS ES+ m/e 457.5 (M+1). 1H NMR (400 MHz, CD2Cl2) δ 8.3 (d, J=2.0 Hz, 1H), 8.0 (s, 1H), 7.7 (dd, J=8.0, 2 Hz, 1H), 7.6 (m, 2H), 7.5(d, J=7.6 Hz, 1H), 7.0 (d, J=8 Hz, 1H), 4.3 (t, J=7.2 Hz, 2H), 4.1 (t, J=5.6 Hz, 2H), 3.6 (m, 4H), 3.1 (t, J=6.8 Hz, 2H), 2.7 (m, 4H), 2.5 (m, 4H), 2.4 (s, 3H).

Workup

  1. customSeal the tube and place in a microwave reactor
  2. customThe crude product is purified with silica gel chromatography
  3. washas eluting solvents

Sources & evidence

ORD record
ord-0e137bbc84a0443eb94f858bfe4e95e7
Source dataset
uspto-grants-2008_05
Patent number
US07368445B2

Reaction notes

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