Diisopropylethylamine → HCID 57650467, compound

HRID 2063461Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.Cl.[Cl:13][C:14]1[CH:31]=[CH:30][C:17]([CH2:18][N:19]2[C:23]([C@H:24]3[CH2:28][CH2:27][CH2:26][NH:25]3)=[N:22][N:21]=[C:20]2[CH3:29])=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[Cl:13][C:14]1[CH:31]=[CH:30][C:17]([CH2:18][N:19]2[C:20]([CH3:29])=[N:21][N:22]=[C:23]2[C@H:24]2[CH2:28][CH2:27][CH2:26][N:25]2[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:11])=[O:10])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 4-chloro-2-fluoro-1-isocyanatobenzene (102.92 mg, 0.6 mmol) in 20 mL of CH2Cl2 at 0° C. was slowly added a solution of the (R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole HCl salt (209.8 mg, 0.6 mmol) and N,N-diisopropylethylamine (0.2091 mL, 1.2 mmol) in dichloromethane (20 mL). The resulting mixture was stirred 0° C. for 30 minutes, then at room temperature overnight. The reaction mixture was treated with sat. aqueous NaHCO3 (10 mL) and brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc with 10% of MeOH) afforded the desired product as white foamy powder (215 mg, 79.9%).

Workup

customat room temperature
customovernight
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customFlash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc with 10% of MeOH)

Sources & evidence

ORD record: ord-bd293a4b789443208af39f4436ac94ca
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288371B2

Reaction notes

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