Tetrahydrofuran → HCID 87617563, compound

HRID 899364Notes

Reaction equation

HRID 899364 reaction equation
C([Li])#[C:2][CH3:3].[C:5]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:37])[C:20]([C:22]2[C:30]3[C:25](=[C:26]([C:31]4[CH:36]=NC=CN=4)[CH:27]=[CH:28][N:29]=3)[NH:24][CH:23]=2)=[O:21])[C@H:15]([CH3:38])[CH2:14]1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[O:39]1CCCC1>>[C:5]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:37])[C:20]([C:22]2[C:30]3[C:25](=[C:26]([C:31]([CH2:36][C:2]#[CH:3])=[O:39])[CH:27]=[CH:28][N:29]=3)[NH:24][CH:23]=2)=[O:21])[C@H:15]([CH3:38])[CH2:14]1)(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5280236HCID 5280236, compoundHCID 178506788HCID 178506788, compound

Product 1

HCID 87617563HCID 87617563, compound

Procedure

Propynyllithium (21 mg) was added to a solution of Example 52 (41 mg) in tetrahydrofuran (5 ml) at −78° C. The reaction was quenched with methanol at −25° C. in 2 hours. After solvents were removed under vaccum, the residue was carried to the further reactions without any purification. I-64, 1-benzoyl-3-(R)-methyl-4-[(7-(2-propynyl)carbonyl-4-azaindol-3-yl)-oxoacetyl]piperazine MS m/z: (M+H)+ Calc'd for C25H22ClN4O4: 477.13; found 477.17. HPLC retention time: 1.46 minutes (column A).

Workup

  1. customThe reaction was quenched with methanol at −25° C. in 2 hours
  2. customAfter solvents were removed under vaccum
  3. customthe residue was carried to the further reactions without any purification

Sources & evidence

ORD record
ord-373b45291b7641ca8fbd66f176276334
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

Loading…