Diethylamine → HCID 11663641, compound

HRID 1685543Notes

Reaction equation

HRID 1685543 reaction equation
[CH:1]1([CH2:6][CH:7]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[C:8]([NH:10][C:11]2[S:12][C:13]([S:16][CH2:17][C:18](O)=[O:19])=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.ON1C(=O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:55]([NH:57][CH2:58][CH3:59])[CH3:56].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]1([CH2:6][CH:7]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[C:8]([NH:10][C:11]2[S:12][C:13]([S:16][CH2:17][C:18](=[O:19])[N:57]([CH2:58][CH3:59])[CH2:55][CH3:56])=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 8021DiethylamineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11662770HCID 11662770, compound

Product 1

HCID 11663641HCID 11663641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionylamino]-thiazol-5-ylsulfanyl}-acetic acid (33 mg, 70.4 mmol) in DMF (0.5 mL) was added 3-hydroxy-1,2,3-benzotriazin-4-(3H)-one (12 mg, 73.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14 mg, 73 mmol). The reaction mixture was stirred at room temperature for 2 hours after which diethyl amine (10 μL, 96.3 mmol) and DIPEA (12 μL, 70.3 mmol) were added. Stirring was continued for 20 hours. The reaction mixture was purified by HPLC (C18, gradient 25%-100% acetonitrile) to give 3-cyclopentyl-N-(5-diethylcarbamoylmethylsulfanyl-thiazol-2-yl)-2-(4-methanesulfonyl-phenyl)propionamide as an oil. Yield: 15 mg (42%). 1H-NMR (CDCl3): δ 7.91 (d, 2H), 7.62 (d, 2H), 7.45 (s, 1H), 3.93 (t, 1H), 3.63 (s, 3H), 3.38 (q, 2H), 3.31 (q, 2H), 3.05 (s, 3H), 2.28-2.21 (m, 1H), 1.97-1.90 (m, 1H), 1.75-1.47 (m, 7H), 1.23-1.11 (m, 8H); HPLC-MS: m/z: 525 (M+1).

Workup

  1. additionwere added
  2. customThe reaction mixture was purified by HPLC (C18, gradient 25%-100% acetonitrile)

Sources & evidence

ORD record
ord-73fae0dca21e42a0a01b7966090eecbc
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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