HCID 69087699, compound → HCID 69087702, compound

HRID 1047058Notes

Reaction equation

HRID 1047058 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]4[N:21]=[CH:22][CH:23]=[CH:24][C:12]=4[N:11]3[C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)=[CH:4][C:3]=1[N+:44]([O-])=O>CO.[Pd]>[NH2:44][C:3]1[CH:4]=[C:5]([C:8]2[N:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]4[N:21]=[CH:22][CH:23]=[CH:24][C:12]=4[N:11]3[C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:33][CH2:34][CH2:35]3)=[CH:28][CH:27]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 69087699HCID 69087699, compound

Product 1

HCID 69087702HCID 69087702, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (50.0 mg) was added to a solution of tert-butyl (1-{4-[2-(4-methyl-3-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (49.1 mg, 0.0799 mmol) in MeOH (5 mL), and the mixture was stirred for 6.5 hours under hydrogen atmosphere. The catalyst was filtered off and washed with MeOH. The combined filtrate and washings were concentrated, and the residue was purified by silica gel column chromatography (EtOAc/hexane=1:2→1:1→2:1→EtOAc) to afford desired product (28.2 mg, 60.4%) as pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.17 (dd, J=7.8, 1.4 Hz, 1H), 8.00 (dd, J=5.0, 1.4 Hz, 1H), 7.39-7.31 (m, 2H), 7.27 (td, J=7.7, 1.5 Hz, 1H), 7.21-6.69 (m, 8H), 6.58 (dd, J=7.8, 4.6 Hz, 1H), 6.52-6.46 (m, 1H), 5.24 (br s, 1H), 3.56 (br s, 2H), 2.63-2.27 (m, 4H), 2.19-2.06 (m, 1H), 2.14 (s, 3H), 1.95-1.74 (m, 1H), 1.38 (br s, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. concentrationThe combined filtrate and washings were concentrated
  4. customthe residue was purified by silica gel column chromatography (EtOAc/hexane=1:2→1:1→2:1→EtOAc)

Sources & evidence

ORD record
ord-b4053ba6275e46d1ad06d5c1b69f1e85
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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