TFA DCM MeOH → N-Hydroxy 2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxamide

HRID 2079820Notes

Reaction equation

HRID 2079820 reaction equation
C(OC([O:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:25][CH:24]3[CH:20]([CH2:21][N:22]([S:26]([C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=4)(=[O:28])=[O:27])[CH2:23]3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11])C)C(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.CO>>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:25][CH:24]3[CH:20]([CH2:21][N:22]([S:26]([C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=4)(=[O:28])=[O:27])[CH2:23]3)[CH2:19]2)=[N:16][CH:17]=1)=[O:11]

Participants

3

Reactant 2

HCID 19108260TFA DCM MeOHHCID 59367582N-(1-isobutoxyethoxy) 2-[5-(naphthalene-2-sulfonyl)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxamide

Product 1

HCID 59367644N-Hydroxy 2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxamideYield 50%

Procedure

To N-(1-isobutoxyethoxy) 2-[5-(naphthalene-2-sulfonyl)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxamide (0.255 g, 0.5 mmol) was added TFA/DCM/MeOH (5 ml, 1:2:2 mixture). The solution was stirred for 2 h, then concentrated under vacuum. The residue was purified by reverse phase HPLC to yield the desired product (95 mg, 50%). LCMS purity >98%, m/z 440 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 2.90 (2H, br s), 3.24 (4H, dd, J=3.3, 10 Hz), 3.45 (2H, dd, J=6.8, 9.8 Hz), 3.61 (2H, dd, J=6.7, 11.4 Hz), 7.62-7.77 (2H, m), 7.83 (1H, dd, J=1.1, 8.5 Hz), 8.06 (1H, d, J=7.8 Hz), 8.13 (1H, d, J=8.8 Hz), 8.17 (1H, d, J=8.2 Hz), 8.47 (1H, s), 8.55 (2H, s), 11.02 (1H, s).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b6a6a9ce98fa4241b9784809ccc26768
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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