4-Chlorobenzaldehyde → HCID 136140454, compound

HRID 1594389Notes

Reaction equation

[CH:1]1([C:5]2[NH:9][N:8]=[C:7]([NH2:10])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[CH3:20][C:21]1(C)OC(=O)CC(=O)[O:22]1>CCO>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[CH2:20][C:21](=[O:22])[NH:10][C:7]3=[N:8][NH:9][C:5]([CH:1]4[CH2:4][CH2:3][CH2:2]4)=[C:6]23)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To 5-cyclobutyl-1H-pyrazol-3-ylamine (1.0 g, 7.3 mmol) in EtOH (20 mL) was added 4-chlorobenzaldehyde (1.1 g, 8.0 mmol) followed by Meldrum's Acid (1.1 g, 8.0 mmol). The reaction mixture was then heated to 75° C. (oil bath). After 30 min, the reaction was cooled to room temperature, the solid was filtered off, and then washed with MeOH (5 mL) and hexanes (10 mL). The solid was collected and dried under reduced pressure to give the title compound (1.3 g, 59% yield) as a colorless solid. 500 MHz 1H NMR (DMSO-d6) d 12.0 (s, 1H), 10.3 (s, 1H), 7.34 (d, J=8.7 Hz, 2H), 7.11 (d, J=8.3 Hz, 2H), 4.20 (dd, J=7.1, 4.2 Hz, 1H), 3.17 (dddd, J=8.7, 8.7, 8.7, 8.7 Hz, 1H), 2.84 (dd, 15.8, 7.1 Hz, 1H), 2.44 (dd, J=16.2, 4.6 Hz, 1H), 2.09-1.87 (m, 4H), 1.83-1.69 (m, 1H), 1.68-1.61 (m, 1H). 13C NMR (125 Mz, DMSO-d6) d 169.8, 149.5, 144.1, 142.8, 131.7, 129.4, 129.2, 101.1, 41.3, 33.9, 31.0, 28.8, 28.4, 18.7. LRMS m/z (APCI+) 303 (M+1).

Workup

temperaturethe reaction was cooled to room temperature
filtrationthe solid was filtered off
washwashed with MeOH (5 mL) and hexanes (10 mL)
customThe solid was collected
customdried under reduced pressure

Sources & evidence

ORD record: ord-a1a4126cb18f438bbb43552b8ac8e54e
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300944B2

Reaction notes

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