Triethylamine → HCID 5272380, compound

HRID 990254Notes

Reaction equation

HRID 990254 reaction equation
[N:1]1([S:7](Cl)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:34])[CH2:25][NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)[N:16]=1.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[NH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:34])[CH2:25][N:26]([S:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)(=[O:9])=[O:8])[CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:19][CH:18]=2)[N:16]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 491938Acetamide, N-[4-(2-amino-4-thiazolyl)phenyl]-2-[(phenylmethyl)amino]-HCID 12798265Morpholine-4-sulfonyl chloride

Product 1

HCID 5272380HCID 5272380, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Morpholinesulfonyl chloride (213 mg, 1.15 mmol) was added (5 min) to an ice-cold solution of N-{4-(2-amino-4-thiazolyl)phenyl}-2-{(phenylmethyl)amino}acetamide.2HCl (450 mg, 1.09 mmol), the corresponding free base has been described in example 2) and Et3N (443 mg, 4.38 mmol) in CH2Cl2 (10.9 mL). The reaction mixture was allowed to warm to room temperature and DMAP (14.0 mg, 0.11 mmol) was added. After standing for 37 h at room temperature, the mixture was dissolved in EtOAc (125 mL). The solution was washed successively with saturated aqueous NaHCO3 (50 mL) and brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. Purification of the resulting residue by flash chromatography (SiO2, EtOAc) gave the title compound (200 mg, 38% yield) as a white solid: M.p. 193-194°; 1H NMR (400 MHz, DMSO-d6) 3 10.02 (s, 1H), 7.73 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.7 Hz, 2H), 7.30-7.41 (m, 5H), 7.01 (s, 2H), 6.89 (s, 1H), 4.59 (s, 2H), 3.91 (s, 2H), 3.58 (t, J=4.6 Hz, 4H), 3.18 (t, J=4.6 Hz, 4H); MS (FAB) m/z 488 (MH)+; Anal. Calcd for C22H25N5O4S2: C, 54.19; H, 5.17; N, 14.36. Found: C, 53.63; H, 5.07; N, 14.34.

Workup

  1. washThe solution was washed successively with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the resulting residue by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-a0f9407d37a6430b86e6804cb19ed62e
Source dataset
uspto-grants-2002_10
Patent number
US06458959B1

Reaction notes

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