Acetic Acid → HCID 178494885, compound

HRID 561881Notes

Reaction equation

[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:47]=[C:48]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[CH:49]=1)[CH2:10][N:11]([CH:44]1[CH2:46][CH2:45]1)[C:12](=[O:43])[CH:13]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][C:34]2[C:39]([Cl:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=2[Cl:42])=[CH:26][CH:25]=1)[CH2:14][NH:15]C(=O)OC(C)(C)C)#[N:2].[N:55]([Sn](CCCC)(CCCC)CCCC)=[N+:56]=[N-:57].C(O)(=O)C.N>C1C(Cl)=CC=C(Cl)C=1.CO.C(Cl)Cl>[NH2:15][CH2:14][CH:13]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][C:34]2[C:35]([Cl:42])=[CH:36][C:37]([CH3:41])=[CH:38][C:39]=2[Cl:40])=[CH:26][CH:25]=1)[C:12]([N:11]([CH:44]1[CH2:45][CH2:46]1)[CH2:10][C:9]1[CH:8]=[C:7]([O:6][CH2:5][CH2:4][CH2:3][C:1]2[NH:57][N:56]=[N:55][N:2]=2)[CH:49]=[C:48]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[CH:47]=1)=[O:43]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of tert-butyl (3-[[3-(3-cyanopropoxy)-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 74 in dichlorobenzene (0.08 M) was added azidotributyltin (2 eq.). The resulting mixture was heated to 150° C. for 22 h. The reaction was quenched with glacial acetic acid (6 eq.) and directly loaded onto a silica gel column packed with 85:15 (v/v) CH2Cl2: 2.0 M NH3 in MeOH. Elution with the same solvent system afforded the title compound as a yellow oil. MS (ESI+): 725.4.

Workup

washElution with the same solvent system

Sources & evidence

ORD record: ord-5b13d84fd9094fc1806b3c6d0092a85a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063105B2

Reaction notes

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