Triethylamine → HCID 59367688, compound

HRID 2079808Notes

Reaction equation

HRID 2079808 reaction equation
CCN=C=NCCCN(C)C.Cl.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23]([NH:26][CH:27]1[CH2:30][N:29]([C:31]2[N:36]=[CH:35][C:34]([C:37](O)=[O:38])=[CH:33][N:32]=2)[CH2:28]1)(=[O:25])=[O:24].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.[O:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH:58]1[O:63][NH2:64]>C(Cl)Cl.C1COCC1>[O:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH:58]1[O:63][NH:64][C:37]([C:34]1[CH:33]=[N:32][C:31]([N:29]2[CH2:28][CH:27]([NH:26][S:23]([C:14]3[CH:15]=[CH:16][C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:13]=3)(=[O:25])=[O:24])[CH2:30]2)=[N:36][CH:35]=1)=[O:38]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 59367663HCID 59367663, compound

Product 1

HCID 59367688HCID 59367688, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

EDCl (90 mg, 0.47 mmol) was added to a solution of 2-{3-[(2-naphthylsulfonyl)amino]azetidin-1-yl}pyrimidine-5-carboxylic acid (150 mg, 0.39 mmol) in DCM (10 ml) and THF (10 ml) at r.t. under N2. Et3N (0.14 ml, 1.02 mmol), HOBt (63 mg, 0.47 mmol) and O-(tetrahydro-pyran-2-yl)-hydroxylamine (55 mg, 0.47 mmol) were added and the reaction stirred at r.t. overnight. The reaction mixture was concentrated in vacuo giving a colourless oil which was dissolved in DCM (20 ml), washed with water (3×20 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound as a white solid (162 mg, 86%). LCMS purity 93%, m/z 484 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customgiving a colourless oil which
  3. washwashed with water (3×20 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b4519fae0f94a13bcc2fcaa5680bcca
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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