1,1'-Carbonyldiimidazole → HCID 11591381, compound

HRID 1173376Notes

Reaction equation

HRID 1173376 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[C:19]2[O:20][C:21]3[C:30]([CH3:31])=[CH:29][C:28]([C:32]([OH:34])=O)=[CH:27][C:22]=3[S:23](=[O:26])(=[O:25])[CH2:24][C:18]=2[CH:17]=[C:16]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:15]=1.[CH:41]1([NH2:44])[CH2:43][CH2:42]1>CN(C=O)C>[ClH:13].[CH:41]1([NH:44][C:32]([C:28]2[CH:29]=[C:30]([CH3:31])[C:21]3[O:20][C:19]4[C:14]([Cl:13])=[CH:15][C:16]([N:35]5[CH2:36][CH2:37][NH:38][CH2:39][CH2:40]5)=[CH:17][C:18]=4[CH2:24][S:23](=[O:25])(=[O:26])[C:22]=3[CH:27]=2)=[O:34])[CH2:43][CH2:42]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 11606047HCID 11606047, compound

Product 1

HCID 11591381HCID 11591381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1′-Carbonyldiimidazole (0.172 g, 11 mmol) was added at 25° C., to a stirred solution of compound of Example 18 (0.3 g, 7 mmol) in dry DMF (10 mL) under nitrogen atmosphere. The reaction mixture was stirred for 2 h, and cyclopropyl amine (0.06 mL, 8.4 mmol) was added. The reaction mixture was stirred at 25° C. for 2 h. Solvent was partially removed and the reaction mixture was diluted with water (50 mL), The solid separated was filtered, washed with water and dried. The product was converted to its hydrochloride salt using methanolic-HCl to obtain the title compound. Yield: 0.15 g (42.5%); 1H NMR (DMSO-d6, 300 MHz): δ 0.56 (s, 2H, CH2), 0.66 (d, 2H, CH2), 2.61 (s, 3H, CH3), 2.82 (bs, 1H, CH), 3.20-3.36 (m, 8H, 4CH2), 5.11 (s, 2H, CH2), 7.14 (d, 1H, Ar), 7.66 (d, 1H, Ar), 8.01 (s, 1H, Ar), 8.13 (s, 1H, Ar), 8.67 (s, 1H, NH); MS: m/e (ES+) 462 (M+1, freebase).

Workup

  1. stirringThe reaction mixture was stirred at 25° C. for 2 h
  2. customSolvent was partially removed
  3. additionthe reaction mixture was diluted with water (50 mL)
  4. customThe solid separated
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-391982942fb043bdabd4384235d2074f
Source dataset
uspto-grants-2010_11
Patent number
US07834052B2

Reaction notes

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