TFA DCM MeOH → N-Hydroxy 2-{6-[methyl(naphthalene-2-sulfonyl)-amino]-3-aza-bicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

HRID 2079785Notes

Reaction equation

HRID 2079785 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:22][CH:21]3[CH:19]([CH:20]3[N:23]([CH3:37])[S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[CH2:18]2)=[N:15][CH:16]=1)=[O:10].C(O)(C(F)(F)F)=O.C(Cl)Cl.CO>>[OH:7][NH:8][C:9]([C:11]1[CH:16]=[N:15][C:14]([N:17]2[CH2:22][CH:21]3[CH:19]([CH:20]3[N:23]([CH3:37])[S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[CH2:18]2)=[N:13][CH:12]=1)=[O:10]

Participants

3

Reactant 2

HCID 19108260TFA DCM MeOHHCID 59367637N-(Tetrahydro-2H-pyran-2-yloxy) 2-{6-[Methyl(naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

Product 1

HCID 59367636N-Hydroxy 2-{6-[methyl(naphthalene-2-sulfonyl)-amino]-3-aza-bicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamideYield 3%

Procedure

To N-(tetrahydro-2H-pyran-2-yloxy) 2-{6-[methyl(naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide was added TFA/DCM/MeOH (5 ml, 1:1:1 mixture). The solution was stirred at r.t. for 2 h. The mixture was then concentrated under reduced pressure, and purified by reverse phase HPLC to yield the title compound (34 mg, 3% yield over 2 steps). LCMS purity >98%, m/z 440 [M−+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 1.55 (1H, m), 2.25 (2H, m), 2.77 (3H, s), 3.58 (2H, m), 3.78 (2H, d, J=11.8 Hz), 7.66-7.84 (2H, m), 7.82 (1H, dd, J=1.8, 8.6 Hz), 8.06 (1H, m), 8.18 (1H, d, J=8.7 Hz), 8.22-8.28 (1H, m), 8.49-8.52 (1H, m), 8.61 (2H, s), 9.01 (1H, br s), 11.05 (1H, br s).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-13a0a516be2e422d82f23aab3edd891a
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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