[2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester → 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[3-(2-methylamino-ethyl)-ureido]-benzamide

HRID 2234678Notes

Reaction equation

HRID 2234678 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[CH:28][NH:27][C:24]3=[N:25][CH:26]=2)=[CH:17][C:16]=1[C:38](=[O:42])[N:39]([CH3:41])[CH3:40])=[O:13])C)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:29]1[C:23]2[C:24](=[N:25][CH:26]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]([NH:14][C:12]([NH:11][CH2:10][CH2:9][NH:7][CH3:6])=[O:13])=[C:16]([CH:17]=3)[C:38]([N:39]([CH3:41])[CH3:40])=[O:42])[CH:22]=2)[NH:27][CH:28]=1

Participants

4

Reactant 1

HCID 57731591[2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 577315655-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[3-(2-methylamino-ethyl)-ureido]-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester (61 mg, 0.103 mmol) was dissolved in 5% trifluoroacetic acid in dichloromethane (15 mL). The mixture was stirred at room temperature for 1 hour. The mixture was concentrated and the residue was purified by preparative HPLC to give 13 mg (26%) of (5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[3-(2-methylamino-ethyl)-ureido]-benzamide. 1H-NMR (250 MHz, d6-DMSO) δ 11.90 (broad s, 1H), 11.04 (s, 1H), 9.15 (s, 1H), 8.64 (d, J=2.0 Hz, 1H), 8.43 (d, J=8.8 Hz, 1H), 8.24 (d, J=2 Hz, 1H), 8.06 (d, J=2.0 Hz, 1H), 7.81 (dd, J=8.8, 2.0 Hz, 1H), 7.72 (s, 1H), 7.61 (dd, J=7.4, 1.6 Hz, 1H), 7.28 (d, J=7.0 Hz, 1H), 7.13 (d, J=7.6 Hz, 1H), 7.06 (t, J=7.5 Hz, 1H), 3.84 (s, 3H), 2.92 (s, 6H), 2.42 (s, 3H); MS: m/z 487.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2e4b247ff57f4e80babe87f0d7e69a09
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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