N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide → HCID 178520345, compound

HRID 1506647Notes

Reaction equation

HRID 1506647 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:13]([NH:23][C:24](=[O:37])[CH2:25][C:26]3[C:30]4=[N:31][C:32]([O:35]C)=[CH:33][CH:34]=[C:29]4[NH:28][CH:27]=3)[CH2:14][C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=3)=[CH:11][N:12]=2)=[CH:4][CH:3]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH:13]([NH:23][C:24](=[O:37])[CH2:25][C:26]3[C:30]4=[N:31][C:32]([OH:35])=[CH:33][CH:34]=[C:29]4[NH:28][CH:27]=3)[CH2:14][C:15]3[CH:16]=[C:17]([F:22])[CH:18]=[C:19]([F:21])[CH:20]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 90281531N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide

Product 1

HCID 178520345HCID 178520345, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 21 (20 mg, 0.038 mmol) and KI (33 mg, 0.2 mmol) in acetic acid (5 mL) was heated in a microwave reactor at 160° C. for 10 min. After cooling to room temperature and removing the volatiles in vacuo, the resulting residue was purified by reverse phase HPLC to yield the title compound. 1H NMR (400 MHz, DMSO) δ 11.89 (s, 1H), 8.53 (d, J=8.5 Hz, 1H), 8.44 (s, 1H), 8.06 (s, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.80 (s, 1H), 7.61 (d, J=8.6 Hz, 2H), 7.02 (s, 1H), 6.86 (m, 3H), 5.10 (m, 1H), 3.20-3.16 (m, 1H), 3.01-2.95 (m, 1H). MS (m/z) 508.9 [M+H]+.

Workup

  1. customremoving the volatiles in vacuo
  2. customthe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a0652af0171f480fb7ffceb20d4e0f43
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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