Triethylamine → HCID 67412426, compound

HRID 909383Notes

Reaction equation

HRID 909383 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:8]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])=[CH:7][C:6]=1[Br:31].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[Br:31][C:6]1[CH:7]=[C:8]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])[CH:9]=[C:10]([O:11][CH2:12][CH3:13])[C:5]=1[O:4][CH2:3][CH2:2][NH:1][S:40]([CH3:39])(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67411190HCID 67411190, compound

Product 1

HCID 67412426HCID 67412426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the product of step c (130.7 mg), triethylamine (93 μl) and methanesulfonyl chloride 21 μl in dichloromethane (3 ml) was stirred for 17 h. The mixture was diluted with dichloromethane and washed with 0.5N aqueous HCl. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC (Method B). Yield: 57.1 mg. MS-ESI: [M+H]+=566.0/568.0; HPLC: Rt=12.49 min. (method 1). Diast. ratio: 4:1

Workup

  1. washwashed with 0.5N aqueous HCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method B)

Sources & evidence

ORD record
ord-0ab2e6280a8b4c66a73165fd7eb78a86
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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