Triethylamine → HCID 178516687, compound

HRID 1268968Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][NH:24][C@@H:25]([CH2:36][CH2:37][C:38]2[NH:39][CH:40]=[C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:42]=2)[C:26](OCC2C=CC=CC=2)=[O:27])=[CH:15]1.C(N(CC)CC)C>C1COCC1>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][N:24]2[C@@H:25]([CH2:36][CH2:37][C:38]3[NH:39][CH:40]=[C:41]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[N:42]=3)[C:26](=[O:27])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=3)[C:10]2=[O:11])=[CH:15]1

Participants

Conditions

Temperature: 20 °C

Procedure

3-trifluoromethyl-phenylisocyanate (11 mg, 1.2 eq.) is added to a solution of benzyl (2S)-2-[(1H-indol-3-ylmethyl)amino]-4-(4-phenyl-1H-imidazol-2-yl)butanoate (23 mg, 1 eq.) in 2 ml of THF. The mixture is stirred for 2 hours at approximately 20° C. then diluted with 2 ml of THF. Aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added, then triethylamine (200 μl). The mixture is stirred for 15 hours at approximately 20° C. then filtered on frit. The filtrate is then concentrated to dryness under reduced pressure at 40° C. (a co-evaporation with dichloromethane is necessary to eliminate the excess triethylamine) in order to produce the expected compound (25 mg, 92% yield).

Workup

additionAminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added
stirringThe mixture is stirred for 15 hours at approximately 20° C.
filtrationthen filtered on frit
concentrationThe filtrate is then concentrated to dryness under reduced pressure at 40° C. (a co-evaporation with dichloromethane

Sources & evidence

ORD record: ord-83f75943b7454b2faace6013fa2c8db2
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199145B2

Reaction notes

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