Acetic Acid → HCID 59713936, compound

HRID 2223074Notes

Reaction equation

HRID 2223074 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[C:25]([O:32][CH3:33])=[N:26][C:27]([O:30][CH3:31])=[N:28][CH:29]=3)[C:16]=2[CH:34]=1.CC(C1C=C(C(C)C)C(S([N:50]=[N+:51]=[N-:52])(=O)=O)=C(C(C)C)C=1)C.C(O)(=O)C>>[N:50]([CH:19]1[N:18]=[C:17]([C:24]2[C:25]([O:32][CH3:33])=[N:26][C:27]([O:30][CH3:31])=[N:28][CH:29]=2)[C:16]2[CH:34]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=2[N:21]([CH3:22])[C:20]1=[O:23])=[N+:51]=[N-:52]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59713805HCID 59713805, compound

Product 1

HCID 59713936HCID 59713936, compoundYield 95%

Procedure

As illustrated in the scheme above and following General Procedure 6, KHMDS (7.0 mL of 0.5 M in toluene, 3.5 mmol), 7-chloro-5-(2,4-dimethoxy-5-pyrimidinyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (1.16 g, 3.35 mmol), trisyl azide (2.60 g, 8.40 mmol) and acetic acid (0.85 mL, 14.8 mmol) were combined. After workup, purification of the crude product by silica gel column chromatography (2:3 hexanes:EtOAc) provided the title compound as a pale yellow solid (1.23 g, 95%). 1H-NMR (CDCl3): δ 8.64 (s, 1H), 7.54 (dd, J=2.3 Hz, J=8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 7.19 (d, J=2.3 Hz, 1H), 4.51 (s, 1H), 4.08 (s, 3H), 3.78 (s, 3H), 3.47 (s, 3H). MS (ESI) (M+H)+388.

Workup

  1. customAfter workup, purification of the crude product by silica gel column chromatography (2:3 hexanes:EtOAc)

Sources & evidence

ORD record
ord-cad935b95bf34d21b4e3348fbf379cb2
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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