Azidotrimethylsilane → HCID 178504260, compound

HRID 2066425Notes

Reaction equation

[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)=[O:20])=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[N:5]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:4]=1)#[CH:2].C[Si]([N:41]=[N+:42]=[N-:43])(C)C>CN(C)C=O.CO>[NH:41]1[C:1]([C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]4[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:21][C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=5)=[O:20])=[CH:16][CH:17]=4)=[CH:9][CH:10]=3)[N:5]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[N:4]=2)=[CH:2][N:43]=[N:42]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of Example 21C (90 mg, 0.180 mmol) in N,N-dimethylformamide (4 ml) and methanol (0.7 ml) under argon was treated with Cu(I)I (5.00 mg, 0.026 mmol) and trimethylsilyl azide (0.249 ml, 1.798 mmol), then heated at 100° C. in an oil bath in a sealed tube for 3 hours. An additional amount of trimethylsilyl azide (0.5 ml) was added and the vial was recapped and heated at 100° C. for 4 hours and then stirred at room temperature for 16 hours. The resulting mixture was partitioned between ethyl acetate and brine, and the organic extract was dried with MgSO4, concentrated and the residue was purified on a 12 gram Silicycle column eluting with 2 to 3% methanol in CH2Cl2 to afford the title compound.

Workup

temperatureheated at 100° C. for 4 hours
customThe resulting mixture was partitioned between ethyl acetate and brine
extractionthe organic extract
dry with materialwas dried with MgSO4
concentrationconcentrated
customthe residue was purified on a 12 gram Silicycle column
washeluting with 2 to 3% methanol in CH2Cl2

Sources & evidence

ORD record: ord-9d5da4541fe049ddb3c32a7cb98b6211
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293738B2

Reaction notes

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