Sodium Azide → HCID 178436992, compound

HRID 1772594Notes

Reaction equation

HRID 1772594 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:21]=[C:22](/[CH:24]=[CH: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](/[CH:24]=[CH: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 117728075(E)-5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)picolinonitrile

Product 1

HCID 178436992HCID 178436992, compound

Procedure

Compound 2c (120 mg, 0.260 mmol) was treated with NaN3 as described in Example 1, Step H. This resulted in 150 mg of crude compound 96, which was then purified by Prep-HPLC under the following conditions: XbridgePrep Shield RP 18, 5 μm, 19*150 mm; mobile phase, water with 0.05% NH4CO3 and CH3CN (30% CH3CN up to 50% in 8 min, up to 100% in 1 min, down to 30% in 1 min); Detector, UV 254 nm. The title compound 96 was obtained as a yellow solid (38.4 mg, 29% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 9.09 (s, 1H), 8.41-8.33 (m, 4H), 7.95-7.56 (m, 8H), 4.50-4.28 (m, 4H), 4.00-3.71 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H22N10O: 503.2 (M+H). Found 503.2.

Workup

  1. customThis resulted in 150 mg of crude compound 96, which
  2. customwas then purified by Prep-HPLC under the following conditions
  3. waitup to 100% in 1 min
  4. waitdown to 30% in 1 min)

Sources & evidence

ORD record
ord-0f73f5c776e44d8f816be3ec43ca0672
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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