HCID 68067477, compound → HCID 69087658, compound

HRID 1047015Notes

Reaction equation

HRID 1047015 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:43])([CH3:42])[CH3:44])[CH2:35][CH2:36][CH2:37]3)=[CH:30][CH:29]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 68067477HCID 68067477, compound

Product 1

HCID 69087658HCID 69087658, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (51.4 mg) was added to a solution of tert-butyl (1-{4-[2-(4-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (51.4 mg, 0.0856 mmol) in MeOH (5 mL), and the mixture was stirred for 4 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 PTLC (CHCl3/MeOH=9:1) to afford desired product (32.0 mg, 65.5%) as an orange solid. 1HNMR (CDCl3) 400 MHz δ: 8.16 (dd, J=7.8, 1.4 Hz, 1H), 8.02-7.97 (m, 1H), 7.46-7.24 (m, 5H), 7.18-7.09 (m, 3H), 6.97-6.91 (m, 1H), 6.83-6.73 (m, 1H), 6.64-6.55 (m, 3H), 6.45 (s, 1H), 5.21 (br s, 1H), 3.70 (br s, 2H), 2.65-2.25 (m, 4H), 2.19-2.05 (m, 1H), 1.94-1.81 (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 PTLC (CHCl3/MeOH=9:1)

Sources & evidence

ORD record
ord-6e25b33b87a643eab0f64da384350fab
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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