HCID 67540685, compound → HCID 25226777, compound

HRID 1422989Notes

Reaction equation

HRID 1422989 reaction equation
FC(F)(F)C(O)=O.C1(C([N:16]2[CH2:20][CH2:19][CH:18]3[CH2:21][N:22]([C:24]4[C:25]5[S:33][C:32]6[CH2:34][CH2:35][CH2:36][CH2:37][C:31]=6[C:26]=5[N:27]=[C:28]([NH2:30])[N:29]=4)[CH2:23][CH:17]23)C)C=CC=CC=1>[OH-].[OH-].[Pd+2].CCO>[NH:16]1[CH2:20][CH2:19][C@@H:18]2[CH2:21][N:22]([C:24]3[C:25]4[S:33][C:32]5[CH2:34][CH2:35][CH2:36][CH2:37][C:31]=5[C:26]=4[N:27]=[C:28]([NH2:30])[N:29]=3)[CH2:23][C@H:17]12

Participants

4

Reactant 1

HCID 67540685HCID 67540685, compound

Product 1

HCID 25226777HCID 25226777, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A 90 mL parr shaker was charged with 4-[1-(1-phenyl-ethyl)-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl]-6,7,8,9-tetrahydro-benzo[4,5]thieno[3,2-d]pyrimidin-2-ylamine trifluoroacetate (synthesized by route described in Example 2, Steps A-E; 0.20 g, 0.4 mmol), Pd(OH)2/C (30% by weight, 0.06 g) and EtOH (3.7 mL). The mixture was submitted to 60 psi H2 with shaking for 36 h. The reaction mixture was filtered through a pad of diatomaceous earth and concentrated to afford the desired compound (0.12 g). MS: 316.1. 1H NMR (400 MHz, CD3OD) 8 ppm 4.47-4.29 (m, 2H), 4.25-4.07 (m, 2H), 3.91-3.80 (m, 1H), 3.54-3.38 (m, 3H), 2.97-2.84 (m, 2H), 2.69-2.61 (m, 2H), 2.41-2.29 (m, 1H), 2.14-2.02 (m, 1H), 2.02-1.86 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7ea71b0f75ce45569b8a61f26bf10fea
Source dataset
uspto-grants-2015_01
Patent number
US08927555B2

Reaction notes

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