Dimethylamine, hydrochloride → HCID 86636023, compound

HRID 448975Notes

Reaction equation

HRID 448975 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][C:14](=O)[CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.C[CH2:18][N:19](C(C)C)[CH:20](C)C.Cl.CNC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][CH:14]([N:19]([CH3:20])[CH3:18])[CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 16743592HCID 16743592, compound

Product 1

HCID 86636023HCID 86636023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a dry flask loaded with 3-(8-chloro-1-iodo-imidazo[1,5-a]pyrazin-3-yl)-cyclobutanone (400.0 mg, 1.15 mmol) in THF (9.0 mL) was added DIEA (0.42 ml, 2.42 mmol), dimethylamine hydrochloride (0.19 g, 2.30 mmol) followed by sodium triacetoxyborohydride (539 mg, 2.42 mmol) at rt. The resulting mixture was stirred at room temperature overnight. The reaction mixture was extracted with aq. Solution of NaHCO3 (2×30 mL). The aq.—layer was back-extracted with EtOAc (2×100 mL), dried (Na2SO4) and concentrated in vacuo to a solid. The material was carried onto the next step without any further purification. MS (ES+): m/z 344.73/345.81 (100/10) [MH+]

Workup

  1. extractionThe reaction mixture was extracted with aq. Solution of NaHCO3 (2×30 mL)
  2. extractionThe aq.—layer was back-extracted with EtOAc (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo to a solid
  5. customThe material was carried onto the next step without any further purification

Sources & evidence

ORD record
ord-f02f10bc82e84c4f850ffb2ba98b7297
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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