Azido(trimethyl)stannane → HCID 178422701, compound

HRID 564960Notes

Reaction equation

[C:1]([C:3]1[CH:39]=[CH:38][C:6]([CH:7]=[CH:8][C:9]([NH:11][CH2:12][C:13]([N:15]([C:17]2[C:18]([Cl:37])=[C:19]([C:33]([Cl:36])=[CH:34][CH:35]=2)[CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=2[N:30]=[C:29]([CH3:32])[CH:28]=[CH:27]3)[CH3:16])=[O:14])=[O:10])=[CH:5][CH:4]=1)#[N:2].C[Sn]([N:44]=[N+:45]=[N-:46])(C)C.ClC1C(N(C)C(=O)CNC(=O)C=CC2C=CC(C(=O)N(CC(=O)NC)C)=CC=2)=CC=C(Cl)C=1COC1C=CC=C2C=1N=C(C)C=C2>C1(C)C(C)=CC=CC=1>[Cl:37][C:18]1[C:17]([N:15]([CH3:16])[C:13](=[O:14])[CH2:12][NH:11][C:9](=[O:10])[CH:8]=[CH:7][C:6]2[CH:38]=[CH:39][C:3]([C:1]3[NH:46][N:45]=[N:44][N:2]=3)=[CH:4][CH:5]=2)=[CH:35][CH:34]=[C:33]([Cl:36])[C:19]=1[CH2:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[C:29]([CH3:32])[CH:28]=[CH:27]2

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 8-[3-[N-(4-cyanocinnamoylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (76 mg) and trimethyltin azide (109 mg) in xylene (1 ml) was heated at 125° C. for 20 hours. After cooled, methanol-chloroform (1:4 V/V, 10 ml) and silica gel (296 mg) was added to the reaction mixture. The resulting suspension was stirred at ambient temperature for one hour. The silica gel was filtered off, and the filtrate was concentrated in vacuo. The residue was purified by preparative thin-layer chromatography eluting with methanol-chloroform (1:6) to afford 8-[2,6-dichloro-3-[N-methyl-N-[4-(5-tetrazolyl)cinnamoylglycyl]amino]-benzyloxy]-2-methylquinoline (40 mg) as a pale yellow glass.

Workup

temperatureAfter cooled
filtrationThe silica gel was filtered off
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by preparative thin-layer chromatography
washeluting with methanol-chloroform (1:6)

Sources & evidence

ORD record: ord-637861a722b0491f860a3f880754cbf5
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169095A

Reaction notes

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