Triethylamine → HCID 178504895, compound

HRID 1428009Notes

Reaction equation

HRID 1428009 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([OH:8])=O)(=[O:4])=[O:3].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[C:46]1([C:52]2[CH:57]=[C:56]([CH:58]3[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]3)[CH:55]=[CH:54][C:53]=2[NH:64][C:65]([C:67]2[NH:68][CH:69]=[C:70]([C:72]#[N:73])[N:71]=2)=[O:66])[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]=1.CCN(CC)CC>C(Cl)Cl>[C:46]1([C:52]2[CH:57]=[C:56]([CH:58]3[CH2:59][CH2:60][N:61]([C:6](=[O:8])[CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:62][CH2:63]3)[CH:55]=[CH:54][C:53]=2[NH:64][C:65]([C:67]2[NH:68][CH:69]=[C:70]([C:72]#[N:73])[N:71]=2)=[O:66])[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 37328412-Methanesulfonylacetic acidHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

Product 1

HCID 178504895HCID 178504895, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A flask was charged with methanesulfonyl-acetic acid (14 mg, 0.10 mmol), EDCI (30 mg, 0.15 mmol), HOBt (14 mg, 0.10 mmol), DIEA (36 μL, 0.20 mmol) and 0.5 mL DCM and stirred at 25° C. After 10 min, a solution containing 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide TFA salt (40 mg, 0.08 mmol) (as prepared in Example 20, step (b)) and NEt3 (14 μL, 0.09 mmol) in 0.5 mL DCM was added and the reaction allowed to proceed for 10 h at 25° C. The reaction mixture was loaded on a 5-g SPE cartridge (silica) and the title compound was eluted with 10% EtOH/EtOAc to give 10 mg (25%) of a white solid. 1H-NMR (400 MHz, CDCl3): δ 11.60 (br s, 1H), 9.52 (s, 1H), 8.30 (d, 1H), 7.74 (s, 1H), 7.60 (dd, 1H), 7.03 (d, 1H), 5.86 (m, 1H), 4.84 (m, 1H), 4.18 (s, 2H), 4.12 (m, 1H), 3.32 (m, 1H), 3.20 (s, 3H), 2.82 (m, 2H), 2.30 (m, 4H), 1.98 (m, 2H), 1.84 (m, 5H), 1.72 (m, 1H). Mass spectrum (ESI, m/z): Calcd. for C25H29N5O4S, 496.2 (M+H). found 496.2.

Workup

  1. additionwas added
  2. waitto proceed for 10 h at 25° C
  3. washthe title compound was eluted with 10% EtOH/EtOAc

Sources & evidence

ORD record
ord-8773a7059b694ddca299bee78ed26cc7
Source dataset
uspto-grants-2015_01
Patent number
US08933091B2

Reaction notes

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