1,1'-Carbonyldiimidazole → HCID 178516993, compound

HRID 1772601Notes

Reaction equation

HRID 1772601 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]=[C:15]([NH2:20])[C:16]([NH2:19])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C1N=CN([C:41](N2C=NC=C2)=[O:42])C=1>C1COCC1>[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]=[C:15]4[N:20]=[C:41]([OH:42])[NH:19][C:16]4=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 117728025(E)-5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridine-2,3-diamine

Product 1

HCID 178516993HCID 178516993, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 6b (220 mg, 0.470 mmol) and CDI (200 mg, 1.23 mmol) in THF (8 mL) was stirred at rt for 18 h. The reaction was quenched with H2O (10 mL). The resulting solids were collected by filtration and washed with Et2O to obtain the title compound 94 as a light yellow solid (57.6 mg, 25% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 11.62 (s, 1H), 11.08 (s, 1H), 8.33 (d, J=8.4 Hz, 1H), 8.21 (s, 1H), 8.11 (s, 1H), 7.97-7.92 (m, 2H), 7.86-7.80 (m, 2H), 7.74 (t, J=7.8 Hz, 1H), 7.66 (s, 1H), 7.60-7.51 (m, 2H), 7.39 (s, 1H), 4.40-4.25 (m, 4H), 3.95-3.75 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C27H22N8O2: 491.2 (M+H). Found 491.0.

Workup

  1. customThe reaction was quenched with H2O (10 mL)
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-40d3341fe62c4ef89ce44fc10954c4e9
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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