Methylamine → HCID 89579438, compound

HRID 928612Notes

Reaction equation

HRID 928612 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([CH:28]1[CH2:31][CH2:30][CH2:29]1)[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:20][S:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:9][CH2:8]1.C[Al](C)C.[CH3:37][NH2:38]>C(Cl)Cl>[CH:28]1([N:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[C:14]4[C:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:20][S:19][C:15]=4[N:16]=[CH:17][N:18]=3)[CH2:11][CH2:12]2)[CH2:4][C:3]([NH:38][CH3:37])=[O:2])[CH2:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 16682925TrimethylaluminumHCID 89579329HCID 89579329, compound

Product 1

HCID 89579438HCID 89579438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction was stirred for min and then allowed to warm to room temperature. After stirring for 30 minutes, methyl-2-[cyclobutyl-[[1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]amino]acetate (37 mg, 0.082 mmol) in DCM (0.5 mL) was added dropwise and the reaction stirred for 2 h. A further 123 μL of trimethylaluminium and a further 123 μL of methylamine were added and the reaction stirred overnight at room temperature. The solvents were then evaporated and the residue purified by column chromatography eluting 0 to 5% v/v of 7 M ammonia/methanol in DCM to give 2-[cyclobutyl-[[1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]amino]-N-methyl-acetamide as a colourless solid (6 mg). LCMS RT=3.01. M+1=450.

Workup

  1. stirringAfter stirring for 30 minutes
  2. stirringthe reaction stirred for 2 h
  3. stirringthe reaction stirred overnight at room temperature
  4. customThe solvents were then evaporated
  5. customthe residue purified by column chromatography
  6. washeluting 0 to 5% v/v of 7 M ammonia/methanol in DCM

Sources & evidence

ORD record
ord-ca02d570969046aab7c036559b1af538
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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