Triethylamine → HCID 57513717, compound

HRID 2368412Notes

Reaction equation

HRID 2368412 reaction equation
[NH2:1][C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6]1[S:7][C:8]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:10]=1)=[O:4].[CH:26]1([CH2:31][C:32](Cl)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(N(CC)CC)C>C(Cl)Cl>[CH:26]1([CH2:31][C:32]([NH:1][C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6]2[S:7][C:8]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)=[O:4])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3485182Cyclopentylacetyl chlorideHCID 57513825HCID 57513825, compound

Product 1

HCID 57513717HCID 57513717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-N-[4-(4-fluoro-phenyl)-5-morpholin-4-yl-thiazol-2-yl]-2-methyl-propionamide (1 eq), cyclopentyl acetyl chloride (1.05 eq) and triethyl amine (3 eq) were stirred as a solution in DCM (5 mL). Desired product was isolated from reaction mixture by silica gel chromatography. LCMS Method 10 Rt=1.48 (M+1=475.1, M−1=473.1), HRMS; expected=474.2101, found=474.2116. 1H NMR (400 MHz, DMSO-D6) 1.07-1.18 (m, 2H) 1.38 (s, 5H) 1.42-1.51 (m, 2H) 1.52-1.60 (m, 2H) 1.62-1.73 (m, 2H) 2.11 (s, 3H) 2.78-2.88 (m, 4H) 3.69-3.78 (m, 4H) 7.23 (t, J=8.91 Hz, 2H) 8.01 (s, 1H) 8.13 (dd. J=8.59, 5.81 Hz, 2H) 11.45 (s, 1H).

Sources & evidence

ORD record
ord-d151c1f175094cc189635ea1dc2961a7
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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