2-Methyl-2-butanol → HCID 67253476, compound

HRID 1961512Notes

Reaction equation

[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.I[C:16]1[CH:28]=[CH:27][C:19]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(O)(CC)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:21]1([CH2:20][C:19]2[CH:18]=[CH:17][C:16]([NH:1][C:2]3[C:6]([C:7]#[N:8])=[CH:5][N:4]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:3]=3)=[CH:28][CH:27]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

Conditions

Temperature: 100 °C

Procedure

3-amino-1-phenyl-1H-pyrazole-4-carbonitrile (100 mg, 0.543 mmol), 4-(4-iodobenzyl)morpholine (165 mg, 0.543 mmol), Pd2dba3 (24.86 mg, 0.027 mmol), K2CO3 (83 mg, 0.597 mmol) and X-Phos (64.7 mg, 0.136 mmol) were added to a 5 mL microwave vial. Degassed tert-amyl alcohol (0.8 mL) was added and the vial was evacuated and back-filled with N2 (×3). The resulting mixture was stirred at 100° C. for 24 hours. Room temperature was attained, MeOH was added and the solvent removed in vacuo while loading onto silica. Purification of the residue by MPLC (0-15% MeOH—CHCl3) gave 3-{[4-(morpholin-4-ylmethyl)phenyl]amino}-1-phenyl-1H-pyrazole-4-carbonitrile as a beige solid.

Workup

customthe vial was evacuated
additionback-filled with N2 (×3)
customRoom temperature
additionMeOH was added
customthe solvent removed in vacuo
customPurification of the residue by MPLC (0-15% MeOH—CHCl3)

Sources & evidence

ORD record: ord-604f677c17474bffb0fc7c049c79ddbb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415346B2

Reaction notes

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