Diisopropylethylamine → HCID 67970587, compound

HRID 889541Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(O)(O)(=O)=O.[NH2:24][C:25]1[NH:26][CH:27]=[CH:28][N:29]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[CH:7][C:3]=1[C:4]([NH:24][C:25]1[NH:26][CH:27]=[CH:28][N:29]=1)=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-chloro-4-methyl-5-[(2-methylpropanoylamino)methyl]benzoic acid (75.0 mg, 0.28 mmol, 1.0 equiv) and 2-aminoimidazole monosulfate (51.4 mg, 0.28 mmol, 1.0 equiv) in DMF (0.56 mL), add DIEA (0.204 mL, 1.17 mmol, 4.2 equiv) and BOP (152 mg, 0.33 mmol, 1.2 equiv). Stir at 60° C. for 5 h and isolate the resulting precipitate by filtration. Triturate with 9:1 dichloromethane:methanol (800 mL), and filter through a pad of silica gel. Concentrate the filtrate under reduced pressure to furnish the title compound as a white solid (57 mg, 61% yield): 1H NMR (DMSO-d6, 400 MHz): δ 11.76 (br s, 2H), 8.20 (t, 1H, J=6.0 Hz), 7.33 and 7.33 (s and s, 1H and 1H, isochronous), 6.75 (br s, 2H), 4.21 (d, 2H, J=5.7 Hz), 2.42 (sep, 1H, J=6.8 Hz), 2.28 (s, 3H), 1.00 (d, 6H, J=6.8 Hz). MS (m/z) (35Cl/37Cl) 335/337 (M+1).

Workup

customisolate the resulting precipitate
filtrationby filtration
customTriturate with 9:1 dichloromethane
filtrationmethanol (800 mL), and filter through a pad of silica gel
concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record: ord-61519d6851434f99a85e93a4f7b7cc20
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252831B2

Reaction notes

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