Ammonia → HCID 178518580, compound

HRID 1034976Notes

Reaction equation

[CH:1]1([C:5]2[C:17]3[C:16]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=4[C:10](=[O:18])[NH:9][C:8]=3[N:7]([CH2:19][C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]#[N:24])[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[N-:28]=[N+:29]=[N-:30].C([Sn](=O)CCCC)CCC.N>C1(C)C=CC=CC=1>[CH:1]1([C:5]2[C:17]3[C:16]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=4[C:10](=[O:18])[NH:9][C:8]=3[N:7]([CH2:19][C:20]3[CH:27]=[CH:26][CH:25]=[C:22]([C:23]4[NH:30][N:29]=[N:28][N:24]=4)[CH:21]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of Example 95A (150 mg) and trimethylsily azide (582 mg) in toluene (20 ml) was added dibutyltin oxide (28 mg). The mixture was heated at 100° C. for 3 days. Solid material was collected by filtration, washed with methanol and dried to give Example 95. Yield: 100 mg. MS (DCI/NH3) m/z 402 (M+H)+; 1H NMR (500 MHz, CD3OD): δ 1.81 (s, 2H), 1.92 (m, 1H), 2.02-2.11 (m, 1H), 2.35-2.44 (m, 4H), 2.51 (m, 2H), 2.91 (br s, 2H), 3.84-3.90 (m, 1H), 5.37 (br s, 1H), 5.51 (s, 2H), 5.51 (s, 2H), 7.30 (m, 2H), 7.97 (m, 2H),

Workup

filtrationSolid material was collected by filtration
washwashed with methanol
customdried
customto give Example 95

Sources & evidence

ORD record: ord-dc99d22a6d6c453eb4fbc5e78ef4ab92
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546368B2

Reaction notes

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