Triethylamine → HCID 58551189, compound

HRID 1908142Notes

Reaction equation

C(N(CC)CC)C.Cl.Cl.[CH3:10][N:11]1[C:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[O:22][C:23]3([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:14]=2[CH:13]=[N:12]1.[CH:29]([S:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][C:36]=1[CH3:44])(=[O:34])=[O:33])([CH3:31])[CH3:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH:29]([S:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39]([N:26]2[CH2:27][CH2:28][C:23]3([C:14]4[CH:13]=[N:12][N:11]([CH3:10])[C:15]=4[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[O:22]3)[CH2:24][CH2:25]2)=[O:40])=[CH:37][C:36]=1[CH3:44])(=[O:34])=[O:33])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 40 °C

Procedure

Triethylamine (152 μL, 1.1 mmol) was added to a mixture of 1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]dihydrochloride (108 mg, 0.33 mmol), 4-(isopropylsulfonyl)-3-methylbenzoic acid (80 mg, 0.33 mmol), HATU (126 mg, 0.33 mmol), and dichloromethane (2 mL) at 25° C. The mixture was heated at 40° C. for 3 h. The mixture was concentrated and the residue was purified by column chromatography (0-100% ethyl acetate/hexanes) to give (4-(isopropylsulfonyl)-3-methylphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (107 mg, 65%) as a fluffy white solid. ESI-MS m/z calc. 479.6. found 480.3 (M+1)+. Retention time: 2.24 minutes (3 min run).

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-b28b69dd4b7e4df79a053f9285acb7bd
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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