Ethyl Acetate → HCID 53354589, compound

HRID 2405104Notes

Reaction equation

HRID 2405104 reaction equation
[CH:1]1([CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([NH:14][C:15](=[O:26])[C:16]4[CH:21]=[CH:20][C:19]([C:22]([OH:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=4)[N:10]=[CH:9][C:8]=3[CH:7]=[CH:6]2)[CH2:3][CH2:2]1.C1C(=O)N([Br:34])C(=O)C1.CCOC(C)=O>C(Cl)Cl>[Br:34][C:7]1[C:8]2[CH:9]=[N:10][C:11]([NH:14][C:15](=[O:26])[C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:25])([CH3:23])[CH3:24])=[CH:20][CH:21]=3)=[CH:12][C:13]=2[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 53354588HCID 53354588, compound

Product 1

HCID 53354589HCID 53354589, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To an ice-cooled solution of N-(1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(2-hydroxypropan-2-yl)benzamide (Example 9, 75 mg, 0.215 mmol) in DCM (4 ml) was added NBS (38.2 mg, 0.215 mmol). The reaction mixture was stirred at 50° C. for 1 h, and then subjected to chromatography (NH—SiO2, EtOAc). The fractions were concentrated in vacuo and purified by preparatory HPLC to give the title compound N-(3-bromo-1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(2-hydroxypropan-2-yl)benzamide (60 mg, 0.14 mmol, 65% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.40-0.48 (m, 2H) 0.52-0.59 (m, 2H) 1.20-1.32 (m, 1H) 1.46 (s, 6H) 4.05 (d, J=7.07 Hz, 2H) 5.17 (s, 1H) 7.59 (d, J=8.59 Hz, 2H) 7.74 (s, 1H) 8.02 (d, J=8.59 Hz, 2H) 8.40 (s, 1H) 8.51 (s, 1H) 10.69 (s, 1H); m.p. 193-194° C.

Workup

  1. concentrationThe fractions were concentrated in vacuo
  2. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-44a977ef6aed42a3a4287dbc8124fc11
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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