Tetrahydrofuran → HCID 178478727, compound

HRID 1272684Notes

Reaction equation

[ClH:1].Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:13]([NH:25][C:26]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=3)[N:12]=2)[CH2:6][CH2:5]1.O1CCCC1.[N:39]([Sn](CCCC)(CCCC)CCCC)=[N+:40]=[N-:41]>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[NH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([NH:10][C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)=[C:13]([NH:25][C:26]3[CH:33]=[CH:32][C:29]([C:30]4[NH:41][N:40]=[N:39][N:31]=4)=[CH:28][CH:27]=3)[N:12]=2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 120 °C

Procedure

296 mg of the product obtained in Example 83 in 3 ml of toluene and 0.26 ml of azido tributyltin are mixed together at ambient temperature then the reaction medium is heated at a temperature of approximately 120° C. for 22 hours then left to return to ambient temperature. 7 ml of tetrahydrofuran is added to the suspension obtained, gaseous hydrochloric acid is bubbled through for 1 minute then nitrogen is bubbled through for 10 minutes, the product obtained is separated, followed by rinsing with ether and drying under reduced pressure at 50° C. In this way 374 mg of expected product is obtained.

Workup

waitthen left
customto return to ambient temperature
customobtained
customgaseous hydrochloric acid is bubbled through for 1 minute
customnitrogen is bubbled through for 10 minutes
customthe product obtained
customis separated
washby rinsing with ether
customdrying under reduced pressure at 50° C

Sources & evidence

ORD record: ord-0c2f668b55554d3ab35a9a7da219fee9
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208598B2

Reaction notes

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