Triethylamine → HCID 23394046, compound

HRID 966149Notes

Reaction equation

[CH3:1][O:2][NH:3][C:4]([C:6]1[CH:7]=[C:8]([NH:13][C:14]2[C:19]3=[C:20]([CH:27]([CH3:29])[CH3:28])[C:21](C(NC)=O)=[CH:22][N:18]3[N:17]=[CH:16][N:15]=2)[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5].C([N:32]([CH2:35]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])C=CC=CC=1.[CH3:54][N:55]1[CH2:59][CH2:58][CH2:57][CH:56]1[CH2:60][CH2:61][OH:62]>O1CCOCC1>[CH3:54][N:55]1[CH2:59][CH2:58][CH2:57][CH:56]1[CH2:60][CH2:61][O:62][C:35](=[O:44])[NH:32][C:21]1[C:20]([CH:27]([CH3:29])[CH3:28])=[C:19]2[N:18]([CH:22]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:13][C:8]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:6]([C:4]([NH:3][O:2][CH3:1])=[O:5])[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To solution of compound A of Example 18 (63 mg, 0.16 mmol) in 1,4-dioxane (1.7 mL) at RT were added 4A sieves, triethylamine (0.91 mmol) and diphenylphosphoryl azide (0.41 mmol). The resulting mixture was warmed to 50° C. for 2 h, then to 80° C. and 2-(1-methylpyrrolidin-2-yl)-ethanol (0.82 mmol) was added. After 2 h, the mixture was cooled RT, filtered and water was added. The mixture was purified by reverse phase preparative HPLC. The appropriate fractions were collected and concentrated. The residue was further purified by silica gel column chromatography eluting with 1% NH4OH, 5% methanol in dichloromethane to afford the title compound (17 mg, 20%). LC/MS; (M+H)+=510.3

Workup

temperaturethe mixture was cooled RT
filtrationfiltered
additionwater was added
customThe mixture was purified by reverse phase preparative HPLC
customThe appropriate fractions were collected
concentrationconcentrated
customThe residue was further purified by silica gel column chromatography
washeluting with 1% NH4OH, 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-4cc4c79d64ff489bb480b6ade2b86d64
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951859B2

Reaction notes

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