Sodium Azide → HCID 178419988, compound

HRID 1772597Notes

Reaction equation

HRID 1772597 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:21]=[C:22]([CH2:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[N-:36]=[N+:37]=[N-:38].[Na+]>>[NH:36]1[C:19]([C:16]2[N:17]=[CH:18][C:13]([C:10]3[N:9]4[CH:21]=[C:22]([CH2:24][CH2:25][C:26]5[CH:35]=[CH:34][C:33]6[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=6)[N:27]=5)[N:23]=[C:8]4[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[N:12][CH:11]=3)=[CH:14][CH:15]=2)=[N:20][N:38]=[N:37]1

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 1177322605-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl) picolinonitrile

Product 1

HCID 178419988HCID 178419988, compoundYield 10%

Procedure

Compound 3b (300 mg, 0.650 mmol) was treated with NaN3 as described in Example 1, Step H to obtain the title compound 77 as a light yellow solid (37.2 mg, 10% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.79 (s, 1H), 8.26 (d, J=8.4 Hz, 1H), 8.15 (d, J=8.1 Hz, 1H), 8.04-8.02 (m, 1H), 7.92 (d, J=8.4 Hz, 2H), 7.80 (s, 1H), 7.70 (t, J=7.2 Hz, 1H), 7.56-7.46 (m, 3H), 4.21-4.09 (m, 4H), 3.75-3.65 (m, 4H), 3.35-3.25 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C27H24N10O: 505.2 (M+H). Found 505.3.

Sources & evidence

ORD record
ord-6766c01e115f4ee784c74c8417081db6
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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