Acetic Acid → HCID 59713771, compound

HRID 2223081Notes

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:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C:16]=2[CH:30]=1.CC(C1C=C(C(C)C)C(S([N:46]=[N+:47]=[N-:48])(=O)=O)=C(C(C)C)C=1)C.C(O)(=O)C>>[N:46]([CH:19]1[N:18]=[C:17]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:16]2[CH:30]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=2[N:21]([CH3:22])[C:20]1=[O:23])=[N+:47]=[N-:48]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 3717072,4,6-Triisopropylbenzenesulfonyl azide

HCID 3251421Potassium bis(trimethylsilyl)amide

HCID 59714070HCID 59714070, compound

Product 1

HCID 59713771HCID 59713771, compoundYield 90.2%

Procedure

As illustrated in the scheme above and following General Procedure 6, KHMDS (10.5 mL of 0.5 M in toluene, 5.25 mmol), 7-chloro-1,3-dihydro-1-methyl-5-(3-pyridinyl)-2H-1,4-benzodiazepin-2-one (1.43 g, 4.99 mmol), trisyl azide (3.86 g, 12.5 mmol) and acetic acid (1.26 mL, 22.0 mmol) were combined. After workup, purification of the crude product by silica gel column chromatography (1:1 CH2Cl2:EtOAc) provided the title compound as a yellow foam (1.47 g, 90%). 1H-NMR (CDCl3): δ 8.80 (s, 1H), 8.76 (d, J=3.6 Hz, 1H), 8.14 (dt, J=1.6 Hz, J=8.0 Hz, 1H), 7.61 (dd, J=2.0 Hz, J=8.4 Hz, 1H), 7.44 (ddd, J=0.8 Hz, J=4.8 Hz, J=8.0 Hz, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.35 (d, J=2.4 Hz, 1H), 4.56 (s, 1H), 3.48 (s, 3H). MS (ESI) (M+H)+=327.

Workup

customAfter workup, purification of the crude product by silica gel column chromatography (1:1 CH2Cl2:EtOAc)

Sources & evidence

ORD record: ord-8e8a0e2eae1044148776e52e9e738e89
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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