Sodium Carbonate → HCID 66603901, compound

HRID 2410820Notes

Reaction equation

HRID 2410820 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)[CH:12]=[C:11]([C:25]([NH2:27])=[O:26])[C:7]=3[NH:8][C:9]=2[CH:10]=1.Cl.Cl[CH2:30][CH2:31][N:32]([CH2:37][CH2:38]Cl)[C:33]([CH3:36])([CH3:35])[CH3:34].C([O-])([O-])=O.[Na+].[Na+]>CC(O)(C)C>[C:33]([N:32]1[CH2:37][CH2:38][N:1]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:14]=[C:13]([C:15]5[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=5)[CH:12]=[C:11]([C:25]([NH2:27])=[O:26])[C:7]=4[NH:8][C:9]=3[CH:10]=2)[CH2:30][CH2:31]1)([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 116236N,N-Bis(2-chloroethyl)-2-methylpropan-2-amine--hydrogen chloride (1/1)HCID 66604922HCID 66604922, compound

Product 1

HCID 66603901HCID 66603901, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 7-amino-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (90 mg, 0.243 mmol), N,N-bis(2-chloroethyl)-2-methylpropan-2-amine hydrochloride (114 mg, 0.486 mmol) and Na2CO3 (129 mg, 1.22 mmol) in t-BuOH (2 mL) was heated at reflux overnight. Purification by HPLC gave 7-(4-tert-butylpiperazin-1-yl)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (40 mg, 0.077 mmol, 32% yield). MS (ESI) m/z 496.2 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.30 (1H, s), 8.60 (2H, d, J=1.53 Hz), 8.56 (1H, br. s.), 8.40 (1H, s), 8.07 (1H, d, J=8.55 Hz), 7.85 (1H, br. s.), 7.74-7.78 (2H, m), 7.20 (1H, d, J=1.83 Hz), 7.00 (1H, dd, J=8.85, 2.14 Hz), 3.23-3.28 (4H, m), 2.71 (4H, d, J=4.27 Hz), 1.08 (9H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-7a8170ae36ba4354bcf7fbc194836a22
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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