Acetyl chloride → HCID 59331379, compound

HRID 1881985Notes

Reaction equation

HRID 1881985 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][C@@H:37]6[CH2:39][C@H:34]5[CH2:35][NH:36]6)=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:40](Cl)(=[O:42])[CH3:41].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:40]([N:36]1[CH2:35][C@@H:34]2[CH2:39][C@H:37]1[CH2:38][N:33]2[CH2:32][C:29]1[CH:30]=[N:31][C:26]([C:24]2[NH:25][C:21]([CH:13]([C:10]3[CH:9]=[CH:8][C:7]([S:4]([CH:1]4[CH2:2][CH2:3]4)(=[O:5])=[O:6])=[CH:12][CH:11]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:22][CH:23]=2)=[CH:27][CH:28]=1)(=[O:42])[CH3:41]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59331325HCID 59331325, compound

Product 1

HCID 59331379HCID 59331379, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,4S)-2-{[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]methyl}-2,5-diazabicyclo[2.2.1]heptane (29.0 mg) in dichloromethane (5 mL) were added acetyl chloride (6 μL) and triethylamine (23 μL) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (10.0 mg, yield 32%) as a colorless amorphous solid. MS: 589 (MH+).

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c90badb1f19347d6bf08bf7aa2281e95
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…