Triethylamine → HCID 69759201, compound

HRID 1883497Notes

Reaction equation

HRID 1883497 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43](=[NH:45])[NH2:44])=[CH:39][CH:38]=2)[C:16]([NH:18][C@@H:19]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:20](=[O:29])[NH:21][CH2:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:17])[CH:12]=[CH:13][CH:14]=1.Cl.[C:47](=[NH:52])(OCC)[CH3:48].C(N(CC)CC)C.C(#N)C.O>CO.C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43](=[NH:44])[NH2:45])=[CH:39][CH:38]=2)[C:16]([NH:18][C@@H:19]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:20](=[O:29])[NH:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:47](=[NH:52])[CH3:48])[CH2:25][CH2:24]2)=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)2×HCID 18373917Acetonitrile--water (1/1)HCID 69759435HCID 69759435, compound

Product 1

HCID 69759201HCID 69759201, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(3-bromo-phenyl)-3-(4-carbamimidoyl-phenyl)-N-{(S)-cyclohexyl-[(piperidin-4-ylmethyl)-carbamoyl]-methyl}-propionamide trifluoracetic acid salt (100 mg, 0.13 mmol, less polar diastereomer), ethyl acetimidate hydrochloride (32 mg, 0.26 mmol), and triethylamine (138 μl, 1.04 mmol) in methanol (40 ml) was stirred for 5 days. During the five days the same amount of triethylamine and ethyl acetimidate hydrochloride was added twice. The reaction mixture was evaporated in vacuo and purified by prep. HPLC (HPLC conditions: Purospher(R)Star HP-18e (10 μM), acetonitrile/water+1% TFA, 10% to 100% acetonitrile) to give 70 mg of the desired product (63% yield). MS m/z: 623.3 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. custompurified by prep

Sources & evidence

ORD record
ord-52ee49f5b1834f058b51efc9c526b08f
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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