1,1'-Carbonyldiimidazole → HCID 86615482, compound

HRID 2197722Notes

Reaction equation

HRID 2197722 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-c4b0e27bc41e414aa0a1998f515e2c46
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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