Trifluoroacetic acid → N-(3-Aminopropyl)-N-[1-[4,5-dihydro-3-methyl-4-oxo-5-(phenylmethyl)isoxazolo[5,4-d]pyrimidin-6-yl]propyl]-4-methylbenzamide

HRID 1794596Notes

Reaction equation

HRID 1794596 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:24]1[N:25]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:26](=[O:34])[C:27]2[C:32]([CH3:33])=[N:31][O:30][C:28]=2[N:29]=1)[CH2:22][CH3:23])[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(C)(C)C.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:24]1[N:25]([CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:26](=[O:34])[C:27]2[C:32]([CH3:33])=[N:31][O:30][C:28]=2[N:29]=1)[CH2:22][CH3:23])[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68827326tert-butyl N-[3-[1-(5-benzyl-3-methyl-4-oxo-[1,2]oxazolo[5,4-d]pyrimidin-6-yl)propyl-(4-methylbenzoyl)amino]propyl]carbamate

Product 1

HCID 9826132N-(3-Aminopropyl)-N-[1-[4,5-dihydro-3-methyl-4-oxo-5-(phenylmethyl)isoxazolo[5,4-d]pyrimidin-6-yl]propyl]-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound from Example 1 Step 6 (60 mg, 0.10 mmol) in CH2Cl2 (2.5 mL) at room temperature was treated with Et3SiH (150 mL) followed by TFA (1.0 mL). The reaction mixture was stirred for 0.5 h then concentrated under vacuum to the desired product as a colorless film (32 mg, 65%); 1H NMR (DMSO-d6) δ 7.62 (s, 1H), 7.25 (m, 7H), 7.22 (s, 1H), 5.77 (d, J=16.5 Hz, 1H), 5.39 (s, 1H), 4.90 (d, J=15.9 Hz, 1H), 3.40 (t, J=7.0 Hz, 2H), 2.92 (s, 3H), 2.54 (s, 3H), 2.09 (m, 1H), 1.92 (m, 1H), 1.91 (m, 1H), 1.89 (t, J=7.0 Hz, 3H), 0.68 (m, 1H); LC/MS (ESI): 474 (M+H)+.

Workup

  1. concentrationthen concentrated under vacuum to the desired product as a colorless film (32 mg, 65%)

Sources & evidence

ORD record
ord-b2ba1b8ec7984d8887fa255ca60afcf5
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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