Hydrochloric Acid → HCID 58775903, compound

HRID 1715335Notes

Reaction equation

HRID 1715335 reaction equation
Cl.[NH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]([CH3:15])[CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][C:20]=1[C:28]([F:31])([F:30])[F:29].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:2][C:3]2[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH3:15])[CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:16][CH:17]=2)=[O:24])=[CH:21][C:20]=1[C:28]([F:29])([F:30])[F:31]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amine

Product 1

HCID 58775903HCID 58775903, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDIC hydrochloride (0.33 mmol, 0.07 g) was added in one portion to a suspension of (4-amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amine Compound 1d (0.25 mmol, 0.06 g), 4-chloro-3-trifluoromethyl-benzoic acid Compound 7a (0.22 mmol, 0.05 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 a crystal of DMAP and Et3N (0.65 mmol, 0.1 mL) were added. The mixture was stirred overnight and produced an orange-yellow suspension. The suspension was poured into water and the aqueous layer was extracted with EtOAc (25 mL). The organic layer was washed with water (2×20 mL), then a solution of 5% NaOH (10 mL) and brine. The organic layer was separated, dried over Na2SO4 and filtered. The solvent was removed in vacuo to yield a residue, which was purified via preparative TLC (15:1 CH2Cl2:MeOH) to provide 4-chloro-N-(4-{[methyl-(tetrahydro-pyran-4-yl)-amino]-methyl}-phenyl)-3-trifluoromethyl-benzamide Compound 7b (0.06 g, 63%) as a pale yellow solid. MS m/e 427 (M+H, 100%).

Workup

  1. customproduced an orange-yellow suspension
  2. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  3. washThe organic layer was washed with water (2×20 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customto yield a residue, which
  9. customwas purified via preparative TLC (15:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-07902c58e4204f56a6d1058a4bc33fc2
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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