N-bromobutanimide → HCID 71134226, compound

HRID 1972979Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([C:24]#[N:25])=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.C1C(=O)N([Br:33])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:33])[C:9]([C:24]#[N:25])=[C:10]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][CH2:16]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of tert-butyl 4-(4-amino-6-cyanopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate (54 mg, 0.158 mmol) in DMF (2 mL), NBS (28.07 mg, 0.158 mmol) was added. The mixture was stirred at 0° C. for 2 h. The mixture was concentrated to dryness. Trituration with acetone afforded product (60 mg, 90%). 1H NMR (400 MHz, DMF-da) 7.52 (s, 1H), 4.42-4.38 (m, 4H), 4.88-4.78 (m, 1H), 2.20-2.08 (m, 4H), 1.62 (s, 9H); LC-MS m/z [M+H]+ 420.9% 422.9, LC-MS RT 3.24 min.

Workup

concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record: ord-062f180a29d04424a9278773758576e7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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