1,2-Dichloroethane → HCID 69018289, compound

HRID 1374863Notes

Reaction equation

HRID 1374863 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15](O)=[O:16])=[C:11]([CH3:18])[N:10]=[C:9]1[C@@:19]([N:23]([CH2:33][CH2:34][CH2:35][NH:36]C(OC(C)(C)C)=O)[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)=[O:25])([CH3:22])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:58]([NH2:60])[CH3:59].C(O)(C(F)(F)F)=O>C(Cl)Cl.C1COCC1>[CH2:58]([NH:60][C:15]([C:12]1[C:13](=[O:14])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([C@@:19]([N:23]([CH2:33][CH2:34][CH2:35][NH2:36])[C:24]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[O:25])([CH3:22])[CH2:20][CH3:21])=[N:10][C:11]=1[CH3:18])=[O:16])[CH3:59]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6341EthylamineHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 21076923HCID 21076923, compound

Product 1

HCID 69018289HCID 69018289, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyl-2-{(R)-[(3-tert-butoxycarbonylamino-propyl)-(1-p-tolyl-methanoyl)-amino]-methyl-propyl}-4-methyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid (100 mg, 0.169 mmol) in CH2Cl2 (1.7 mL) was added EDC (36 mg, 0.186 mmol), HOBt (25 mg, 0.186 mmol), TEA (28 uL, 0.203 mmol) followed by ethylamine (85 uL of a 2.0M solution in THF, 0.169 mmol). The reaction mixture was stirred at ambient temperature for 16 h, then TFA (1 mL) was added. After 3 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by reverse phase HPLC to give 47 mg (53%) of 2-{(R)-[(3-amino-propyl)-(1-p-tolyl-methanoyl)-amino]-methyl-propyl}-1-benzyl-4-methyl-6-oxo-1,6-dihydro-pyrimidine-5carboxylic acid ethylamide as a pale yellow solid: MS (ES) m/e 518.4 (M+H)+.

Workup

  1. waitAfter 3 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ed135ec5152a45849877bd7498e858b8
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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