1,1'-Carbonyldiimidazole → HCID 136119390, compound

HRID 2217128Notes

Reaction equation

HRID 2217128 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].NCC1[CH:37]=[CH:36][C:18]([C:19]([N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[NH:25][C:24]3[N:32]([CH3:35])[N:33]=[CH:34][C:23]=3[CH2:22]2)=[O:20])=[CH:17][C:16]=1[CH3:38].CN1[CH2:46][CH2:45][CH2:44]NCC1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:35][N:32]1[C:24]2[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:21]([C:19](=[O:20])[C:18]3[CH:36]=[CH:37][C:11]([CH2:12][NH:8][C:1]([N:3]4[CH2:46][CH2:45][CH2:44][N:5]([CH3:4])[CH2:6][CH2:7]4)=[O:2])=[C:16]([CH3:38])[CH:17]=3)[CH2:22][C:23]=2[CH:34]=[N:33]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 135829584HCID 135829584, compound

Product 1

HCID 136119390HCID 136119390, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1,1′-Carbonyldiimidazole (37 mg, 0.23 mmol) was added to a solution of 5-(4-(aminomethyl)-3-methylbenzoyl)-1-methyl-4,10-dihydropyrazolo-[5,4-b][1,5]benzodiazepine (75 mg, 0.22 mmol) in DMF (2 ml). The solution was stirred for 1 h, a solution of 1-methylhomopiperazine (27 mg, 0.24 mmol) and DIEA (31 mg, 0.24 mmol) in DMF (1 ml) was added and stirring was continued for 24 h. The mixture was concentrated in vacuo and the residue was purified by chromatography on silica gel (eluant 30/2/1-1/1/1 chloroform/methanol/concentrated ammonia) to give a white solid identified as 1-methyl-5-(3-methyl-4-(4-methylperhydro-1,4-diazepine-1-carbonylaminomethyl)benzoyl)-4,10-dihydropyrazolo[5,4-b][1,5](38 mg, 36%).

Workup

  1. stirringstirring
  2. waitwas continued for 24 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel (eluant 30/2/1-1/1/1 chloroform/methanol/concentrated ammonia)
  5. customto give a white solid

Sources & evidence

ORD record
ord-e844be73b3ae4972a5056083715c252d
Source dataset
uspto-grants-2008_08
Patent number
US07407949B2

Reaction notes

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