Dichloromethane → N-Hydroxy 2-{6-[(naphthalene-2-sulfonyl)-(2-pyrrolidin-1-yl-ethyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

HRID 2079787Notes

Reaction equation

HRID 2079787 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]([S:31]([C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=3)(=[O:33])=[O:32])[CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[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]([S:31]([C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=3)(=[O:33])=[O:32])[CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:18]2)=[N:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59367676N-(Tetrahydro-2H-pyran-2-yloxy) 2-{6-[(naphthalene-2-sulfonyl)-(2-pyrrolidin-1-ylethyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

Product 1

HCID 59367588N-Hydroxy 2-{6-[(naphthalene-2-sulfonyl)-(2-pyrrolidin-1-yl-ethyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamideYield 30.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(tetrahydro-2H-pyran-2-yloxy) 2-{6-[(naphthalene-2-sulfonyl)-(2-pyrrolidin-1-ylethyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide (0.234 g, 0.38 mmol) was added TFA:DCM:MeOH (6 ml, 1:1:1 mixture). The mixture was stirred for 3 h at r.t. and then concentrated in vacuo. The product was purified by reverse phase HPLC to yield the title compound (60 mg, 30%). LCMS Purity >98%, m/z 523.25 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 1.55-1.68 (4H, m), 1.78 (1H, m), 2.25-2.34 (2H, m), 2.35-2.45 (4H, m), 2.55-2.65 (2H, m), 3.25-3.42 (5H, m), 3.54-3.63 (2H, m), 3.73-3.85 (2H, m), 7.65-7.77 (2H, m), 7.86 (1H, d, J=8.5 Hz), 8.06 (1H, d, J=7.3 Hz), 8.17 (1H, d, J=7.3 Hz), 8.24 (1H, d, J=7.3 Hz), 8.55 (1H, s), 8.61 (2H, s), 9.00 (1H, br s), 11.05 (1H, br s).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8c0a15e72cc740f783b17bb5f74a7c15
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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