Methylamine → HCID 18428682, compound

HRID 1279635Notes

Reaction equation

HRID 1279635 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[C:8](O)=[O:9])[CH3:3].C1C=CC2N(O)N=[N:29][C:27]=2C=1.C(N(CC)CC)C.CN>C(Cl)Cl>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[C:8]([NH:29][CH3:27])=[O:9])[CH3:3]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 18428670HCID 18428670, compound

Product 1

HCID 18428682HCID 18428682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from example 158 (480 mg, 1.51 mmol) WSCDI (377 mg, 2 mmol), HOBt.H2) (255 mg, 1.66 mmol) and triethylamine (0.53 mL, 3.78 mmol) were dissolved in DCM (0.03 M). After stirring for 30 min, MeNH2 (condensed, 2 mL) was added and the mixture stirred for a further 12 h. The mixture was then evaporated and the residue partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (3 times). The combined organic layers were dried (MgSO4) and evaporated to a yellow oil, which was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (93:7:1)]. The desired title amide was isolated as its hydrochloride salt (285 mg, 63%); Free base: δH(CDCI3, 400 MHz) 2.12 (6 H, s), 2.41 (3 H, s), 2.92 (3 H, d), 3.46 (3 H, s), 6.78 (1 H, brd), 6.84 (2 H, d), 7.20 (2 H, d), 7.63 (1 H, dd), 7.82 (1 H, d); MS m/z (ES+) 331 (MH+)

Workup

  1. stirringthe mixture stirred for a further 12 h
  2. customThe mixture was then evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer re-extracted with ethyl acetate (3 times)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated to a yellow oil, which
  8. customwas purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (93:7:1)]

Sources & evidence

ORD record
ord-cbb4c296359a4a3fa8e676b402939ab1
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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