Acetic Acid → HCID 59714395, compound

HRID 2223078Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][N:18]=[C:17]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C:16]=2[CH:29]=1.CC(C1C=C(C(C)C)C(S([N:45]=[N+:46]=[N-:47])(=O)=O)=C(C(C)C)C=1)C.C(O)(=O)C>>[N:45]([CH:19]1[N:18]=[C:17]([C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[C:16]2[CH:29]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=2[N:21]([CH3:22])[C:20]1=[O:23])=[N+:46]=[N-:47]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 3717072,4,6-Triisopropylbenzenesulfonyl azide

HCID 3251421Potassium bis(trimethylsilyl)amide

HCID 10469503HCID 10469503, compound

Product 1

HCID 59714395HCID 59714395, compoundYield 98%

Procedure

As illustrated in the scheme above and following General Procedure 6, KHMDS (10.4 mL of 0.5 M in toluene, 5.20 mmol), 7-chloro-1,3-dihydro-1-methyl-5-(3-thienyl)-2H-1,4-benzodiazepin-2-one (1.44 g, 4.95 mmol), trisyl azide (3.83 g, 12.4 mmol) and acetic acid (1.25 mL, 21.8 mmol) were combined. After workup, purification of the crude product by silica gel column chromatography (7:3 hexanes:EtOAc) provided the title compound as a pale yellow solid (1.60 g, 98%). 1H-NMR (CDCl3): δ 7.61-7.55 (m, 4H), 7.40 (dd, J=2.9 Hz, J=5.1 Hz, 1H), 7.33 (dd, J=1.0 Hz, J=8.2 Hz, 1H), 4.54 (s, 1H), 3.44 (s, 3H). MS (ESI) (M+H)+=332.

Workup

customAfter workup, purification of the crude product by silica gel column chromatography (7:3 hexanes:EtOAc)

Sources & evidence

ORD record: ord-1820328f806245eb9a3893bd5e5bf980
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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