Triethylamine → HCID 72335616, compound

HRID 2265940Notes

Reaction equation

HRID 2265940 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=1.C(N(CC)CC)C.[N:25]1([C:31]2[N:36]=[CH:35][C:34]([CH:37]=[CH:38][C:39](O)=[O:40])=[CH:33][CH:32]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C1COCC1.CCOC(C)=O>[C:16]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([F:10])[C:7]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:3][NH:2][C:39](=[O:40])[CH:38]=[CH:37][C:34]1[CH:35]=[N:36][C:31]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[CH:32][CH:33]=1)#[CH:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 68786509HCID 68786509, compoundHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride

Product 1

HCID 72335616HCID 72335616, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (20 mg, 0.072 mmol) was suspended in THF and treated with triethylamine (11 mg, 0.108 mmol) and then the resulting mixture was stirred for 10 mins. 3-(6-morpholin-4-yl-pyridin-3-yl)-acrylic acid (17 mg, 0.072 mmol) was added to the reaction mixture followed by DMTMM (22 mg, 0.08 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat'd NaHCO3 (×2), brine, and then dried over anh. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized (CH2Cl) to yield the title compound (8 mg, 24%).

Workup

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. washThe resulting solution was washed successively with water, sat'd NaHCO3 (×2), brine
  3. dry with materialdried over anh. Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was recrystallized (CH2Cl)

Sources & evidence

ORD record
ord-37ade40ab5664276bbfad65af431c44c
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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