Acetic Anhydride → HCID 86636298, compound

HRID 541959Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:43]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(N(CC)C(C)C)(C)C.[C:53](OC(=O)C)(=[O:55])[CH3:54].[OH-].[Na+]>O1CCCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[C:53]([N:40]1[CH2:41][CH2:42][N:37]([C:29]2[CH:30]=[CH:31][C:32]3[NH:33][C:34]4[N:35]=[C:19]([NH:20][C:21]5[CH:22]=[CH:23][CH:24]=[C:25]([CH:43]=5)[CH2:26][CH2:27][C:28]=2[CH:36]=3)[N:18]=[CH:17][C:16]=4[Cl:15])[CH2:38][CH2:39]1)(=[O:55])[CH3:54]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 6-chloro-12-piperazin-1-yl-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene bis(trifluoroacetate) (20 mg, 32 μmol) and N,N-diisopropylethylamine (27 μL, 0.16 mmol) in tetrahydrofuran (0.5 mL) was treated with acetic anhydride (15 μL, 0.16 mmol) and stirred at 20° C. for 16 h. The reaction mixture was treated with 2 M sodium hydroxide (0.16 mL, 0.32 mmol) and stirred at 20° C. for 16 h to remove the undesired acetamide. The reaction mixture was purified by preparative LCMS to give the desired product (10 mg, 47%) as a solid. LCMS for C24H26ClN6O (M+H)+: m/z=449.0.

Workup

stirringstirred at 20° C. for 16 h
customto remove the undesired acetamide
customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record: ord-4bc817cdf8874082b8ec9aefd8370857
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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