Dimethylamine, hydrochloride → HCID 178483588, compound

HRID 64322Notes

Reaction equation

HRID 64322 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C:8]2[NH:11][C:12]3[N:13]([N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:22][CH:21]=4)[C:16]=3[C:17]([NH2:19])=[O:18])[C:7]=2[CH2:6]1)(=[O:4])[CH:2]=C.[CH3:33][O-].[Na+].Cl.[CH3:37][NH:38][CH3:39]>CO>[CH3:37][N:38]([CH3:33])[CH2:39][CH2:2][C:1]([N:5]1[CH2:10][CH2:9][C:8]2[N:11]3[N:14]=[C:15]([C:20]4[CH:21]=[CH:22][C:23]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:24][CH:25]=4)[C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[NH:13][C:7]=2[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 10942334Sodium MethoxideHCID 178459953HCID 178459953, compound

Product 1

HCID 178483588HCID 178483588, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-acryloyl-2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5′,1′:2,3]imidazo[4,5-c]pyridine-3-carboxamide (6 mg, 0.014 mmol) in 5 mL of MeOH at RT was added NaOMe (15 mg, 0.28 mmol) followed by dimethylamine hydrochloride (12 mg, 014 mmol), then the mixture was stirred at 50° C. overnight. After cooling down to RT, the mixture was concentrated. The residue was purified by pre-HPLC eluting from 0% to 60% CH3CN in H2O. Fractions containing the desired product were combined and lyophilized overnight to give 2.5 mg (35%) of 6-(3-(dimethylamino)propanoyl)-2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]pyridine-3-carboxamide as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 11.84-11.82 (m, 1H), 9.55 (s, 1H), 7.69-7.66 (m, 2H), 7.44 (d, J=7.6 Hz, 1H), 7.42 (d, J=7.6 Hz, 1H), 7.18 (t, J=7.6 Hz, 1H), 7.10-7.04 (m, 4H), 4.75-4.72 (m, 2H), 3.87-3.82 (m, 2H), 3.02-3.00 (m, 2H), 2.84-2.78 (m, 2H), 2.77 (s, 6H), 2.71-2.68 (m, 2H). MS (ESI) m/e [M+1]+ 472.9.

Workup

  1. temperatureAfter cooling down to RT
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified
  4. washby pre-HPLC eluting from 0% to 60% CH3CN in H2O
  5. additionFractions containing the desired product
  6. waitlyophilized overnight

Sources & evidence

ORD record
ord-481c27e5fd534285a5ac3ab757f5dfd7
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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