Triethylamine → HCID 11621474, compound

HRID 577775Notes

Reaction equation

HRID 577775 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[C:17]2[C:28]([CH3:29])=[N:27][N:26]([CH3:30])[C:18]2=[N:19][C:20]=1[NH:21][CH2:22][CH:23]1[CH2:25][CH2:24]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.C(N(CC)CC)C.[CH:47]1([C:50](Cl)=[O:51])[CH2:49][CH2:48]1>C1COCC1.C(OCC)(=O)C>[F:38][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[C:17]2[C:28]([CH3:29])=[N:27][N:26]([CH3:30])[C:18]2=[N:19][C:20]=1[N:21]([CH2:22][CH:23]1[CH2:24][CH2:25]1)[C:50]([CH:47]1[CH2:49][CH2:48]1)=[O:51])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 57444438HCID 57444438, compound

Product 1

HCID 11621474HCID 11621474, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-cyclopropylmethyl-amine (0.25 g, 0.45 mmol), triethylamine (0.13 g, 1.3 mmol), and cyclopropanecarbonyl chloride (0.28 g, 2.7 mmol) in THF (5 mL) was prepared in 10 mL reaction vessel and irradiated with 250 Watt microwave power, under 250 psi at 80° C. for 2 h. The vessel was cooled to RT and the reaction mixture was diluted with ethyl acetate (100 mL). The ethyl acetate layer was washed with water (3×100 mL), the organic layer was separated out, dried over sodium sulfate, and concentrated. The resulting oil was purified by column chromatography using silica gel (230-400 mesh) and eluting the column with 1% methanol in dichloromethane afforded a colorless solid (0.147 g), yield: 52.5%, mp 120-122° C.

Workup

  1. customwas prepared in 10 mL reaction vessel
  2. customirradiated with 250 Watt microwave power, under 250 psi at 80° C. for 2 h
  3. washThe ethyl acetate layer was washed with water (3×100 mL)
  4. customthe organic layer was separated out
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting oil was purified by column chromatography
  8. washeluting the column with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-3eade6c6d8a5431b8dbdea3b8e3b9ca5
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

Loading…