1-Hydroxybenzotriazole → HCID 59367593, compound

HRID 2079804Notes

Reaction equation

HRID 2079804 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:19][CH:18]2[CH:16]([CH:17]2[NH:20][C:21]2[N:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][N:22]=2)[CH2:15]1)(=[O:13])=[O:12].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[O:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH:53]1[O:58][NH2:59]>C(Cl)Cl.C1COCC1.CCN(CC)CC>[O:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH:53]1[O:58][NH:59][C:27]([C:24]1[CH:23]=[N:22][C:21]([NH:20][CH:17]2[CH:16]3[CH:18]2[CH2:19][N:14]([S:11]([C:2]2[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=2)(=[O:12])=[O:13])[CH2:15]3)=[N:26][CH:25]=1)=[O:28]

Participants

8

Reactant 4

HCID 757711-Hydroxybenzotriazole2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine2×HCID 59367678HCID 59367678, compound

Product 1

HCID 59367593HCID 59367593, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

To a solution of 2-{[3-(2-naphthylsulfonyl)-3-azabicyclo[3.1.0]hex-6-yl]amino}pyrimidine-5-carboxylic acid (105 mg, 0.26 mmol) in DCM (5 ml) and THF (5 ml) was added EDCl (59 mg, 0.3 mmol). Et3N (0.08 ml, 0.8 mmol) was added followed by HOBt (42 mg, 0.3 mmol) and O-(tetrahydro-pyran-2-yl)-hydroxylamine (36 mg, 0.3 mmol). The suspension was stirred at r.t. for 3 days. Further EDCl (14 mg), Et3N (0.02 ml), HOBt (11 mg), and O-(tetrahydro-pyran-2-yl)-hydroxylamine (9 mg) were added and stirring at r.t. continued for a further 3 days. The reaction mixture was evaporated to dryness, re-dissolved in EtOAc (20 ml) and washed with sat. aq. NaHCO3 (10 ml) and water (10 ml). The EtOAc layer was dried (Na2SO4), filtered and concentrated to dryness to afford the title compound as a white solid (110 mg, 83%). LCMS purity 90%, m/z 511 [M+H]+.

Workup

  1. stirringstirring at r.t.
  2. waitcontinued for a further 3 days
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionre-dissolved in EtOAc (20 ml)
  5. washwashed with sat. aq. NaHCO3 (10 ml) and water (10 ml)
  6. dry with materialThe EtOAc layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-53ac67fc8f074e30a80aa0c4dffde790
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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