Cyclopropylamine → HCID 178489403, compound

HRID 1865636Notes

Reaction equation

HRID 1865636 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[N:24][NH:23][C:20]3=[N:21][CH:22]=2)=[CH:13][C:7]=1[C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[O:4].[CH:34]1([NH2:37])[CH2:36][CH2:35]1>ClCCl>[CH:34]1([NH:37][CH2:2][C:3]([NH:5][C:6]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:25]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[O:32][CH3:33])=[N:24][NH:23][C:20]4=[N:21][CH:22]=3)=[CH:13][C:7]=2[C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[O:4])[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 178489402HCID 178489402, compound

Product 1

HCID 178489403HCID 178489403, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 mg (39 μmol) of 2-(2-bromo-acetylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo-[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 3 mL of dichloromethane. 14 μL (12 mg, 0.2 mmol) of cyclopropylamine was added at room temperature and the resulting mixture left at ambient temperature for 19 h. The resulting solution was evaporated and the residue purified by mass-triggered reverse-phase HPLC to afford 7.1 mg (15 μmol, 38%) of 2-(2-cyclopropylamino-acetylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 13.82 (s, 1H), 10.00 (s, 1H), 8.87 (d, 1H), 8.35 (d, 1H), 8.33 (d, 1H), 7.82 (dd, 1H), 7.72 (d, 1H), 7.65 (dd, 1H), 7.47 (dd(m), 1H), 7.23 (d(m), 1H), 7.11 (ddd, 1H), 3.84 (s, 3H), 3.30 (s, 2H), 3.04 (s, 3H), 2.94 (s, 3H), 2.17 (m, 1H), 0.40 (m, 2H), 0.32 (m, 2H), MS: m/z 485.2 (M+H+).

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-9ab5d008195449e383457234230f7777
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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