Triethylamine → HCID 58775940, compound

HRID 1715338Notes

Reaction equation

HRID 1715338 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]([CH3:14])[CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:17][N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[C:27](O)=[O:28].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[CH3:14][N:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:27]([C:19]2[N:18]([CH3:17])[C:26]3[C:21]([CH:20]=2)=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:28])=[CH:16][CH:15]=1)[CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 757711-HydroxybenzotriazoleHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amine

Product 1

HCID 58775940HCID 58775940, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDIC (0.33 mmol, 0.07 g) was added in one portion to a mixture of (4-amino-benzyl)-methyl-(tetrahydro-pyran -4-yl)-amine Compound 1d (0.25 mmol, 0.06 g), 1-methyl-1H-indole-2-carboxylic acid Compound 12a (0.22 mmol, 0.04 g) and HOBt (0.22 mmol, 0.03 g) in DMF (5.0 mL) at 0° C. The resulting suspension was warmed to r.t. and then a crystal of DMAP and Et3N (0.65 mmol, 0.11 mL) was added and the reaction mixture was stirred overnight. The resulting orange-yellow suspension was poured in water and was extracted with EtOAc (25 mL). The organic layer was washed with water (2×20 mL) followed by 5% NaOH solution (10 mL) and brine. The organic layer was separated, dried over Na2SO4 and filtered. The solvent was removed in vacuo and the resulting residue was purified by preparative TLC (15:1 CH2Cl2/MeOH) to yield 1-methyl-1H-indole-2-carboxylic acid (4-{[methyl-(tetrahydro-pyran -4-yl)-amino]-methyl}-phenyl)-amide Compound 12b as a pale yellow solid (0.05 g, 60%). MS m/e 378 (M+H, 100%).

Workup

  1. extractionwas extracted with EtOAc (25 mL)
  2. washThe organic layer was washed with water (2×20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe resulting residue was purified by preparative TLC (15:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-d5702e7a875c4d71808dd6f741397eee
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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