1,1'-Carbonyldiimidazole → HCID 86615482, compound

HRID 2358557Notes

Reaction equation

HRID 2358557 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6]([NH:15][C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=3[S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:7]([C:12]([OH:14])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:43][NH:44][O:45][CH3:46]>CN(C=O)C>[CH3:46][O:45][N:44]([CH3:43])[C:12]([C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[CH:4][CH:3]=[C:2]([CH3:1])[N:11]=2)=[O:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68461313HCID 68461313, compound

Product 1

HCID 86615482HCID 86615482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 11a (50.5 mg, 0.125 mmol) was reacted with 1,1′-carbonyldiimidazole (40.8 mg, 0.215 mmol) in 2 mL of DMF under an atmosphere of N2 for 30 min. Added N,O-dimethylhydroxylamine hydrochloride (25 mg, 0.215 mmol) and stirred ate room temperature for 24 h. The solvent was concentrated under vacuum giving the title compound. After purification of the crude product by HPLC with AA the product was isolated as the free base (12 mg, 21%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.23 (s, 3H) 2.67 (s, 3H) 2.89 (s, 3H) 3.39 (s, 3H) 6.86 (s, 1H) 6.91-7.04 (m, 1H) 7.15-7.35 (m, 7H) 7.44 (d, J=8.46 Hz, 1H) 8.34 (d, J=8.09 Hz, 1H) 8.67 (s, 1H); MS (ESI+) m/z 445 (M+H)+, 467 (M+Na)+, MS (ESI−) m/z 443 (M−H)−.

Workup

  1. concentrationThe solvent was concentrated under vacuum

Sources & evidence

ORD record
ord-591b9a34cce94afe9611368a3fa6cf23
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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