tert-Butanol → HCID 57962653, compound

HRID 541757Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([CH:26]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[C:16](C(O)=O)[CH:15]=3.C([N:29]([CH2:32]C)CC)C.C1C=CC([O:40]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.[C:53]([OH:57])([CH3:56])([CH3:55])[CH3:54]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([CH:26]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[C:16]([NH:29][C:32](=[O:40])[O:57][C:53]([CH3:56])([CH3:55])[CH3:54])[CH:15]=3

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 6-chloro-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-11-carboxylic acid (9.2 mg, 25.1 μmol) in tert-butyl alcohol (0.16 mL) was added triethylamine (3.5 μL, 25.1 μmol) and diphenylphosphonic azide (5.4 μL, 25.1 μmol). The resulting mixture was heated at 85° C. overnight. The reaction mixture was diluted with DMSO and purified with preparative LCMS to give the desired product (6 mg, 55%). 1H NMR (400 MHz, DMSO-d6): δ 9.33 (s, 1H), 9.22 (s, 1H), 8.09 (s, 1H), 7.92 (s, 1H), 7.31 (m, 2H), 7.08 (t, 1H), 7.03 (s, 1H), 6.88 (dd, 1H), 6.80 (dd, 1H), 2.80 (d, 4H), 1.46 (s, 9H). LCMS calculated for C23H25ClN5O2(M+H)+: m/z=438.2.

Workup

custompurified with preparative LCMS

Sources & evidence

ORD record: ord-069317e56b5741c08300fe54a2d3dbb5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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