Acetyl chloride → HCID 11547245, compound

HRID 253031Notes

Reaction equation

HRID 253031 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[S:19][C:18]3[C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[N:16][C:15]([C:26]4[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=4)=[N:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41]>ClCCl>[OH:32][C:28]1[CH:27]=[C:26]([C:15]2[N:16]=[C:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[C:18]3[S:19][C:11]([CH2:10][N:7]4[CH2:6][CH2:5][CH:4]([NH:3][C:40](=[O:42])[CH3:41])[CH2:9][CH2:8]4)=[CH:12][C:13]=3[N:14]=2)[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66857667HCID 66857667, compound

Product 1

HCID 11547245HCID 11547245, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-[6-(4-Amino-piperidin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-phenol di-hydrochloride salt (80 mg, 0.16 mmol) in dichloromethane (1.5 mL) and triethylamine (5 eq., 110 μL) was added acetyl chloride (2.5 eq., 29 μL). After stirring at rt for 2 hours, the reaction mixture was diluted with dichloromethane, washed with brine, separated and dried (MgSO4). The crude product was evaporated in vacuo, re-dissolved in methanol (2 mL), to this was added sodium carbonate. The reaction mixture was stirred at RT overnight, evaporated in vacuo, diluted with dichloromethane, washed with brine, separated and dried (MgSO4). The residue was purified by chromatography to give the title compound as a white solid (55 mg).

Workup

  1. washwashed with brine
  2. customseparated
  3. dry with materialdried (MgSO4)
  4. customThe crude product was evaporated in vacuo
  5. dissolutionre-dissolved in methanol (2 mL)
  6. additionto this was added sodium carbonate
  7. stirringThe reaction mixture was stirred at RT overnight
  8. customevaporated in vacuo
  9. additiondiluted with dichloromethane
  10. washwashed with brine
  11. customseparated
  12. dry with materialdried (MgSO4)
  13. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-b843ea9ba09f4dbf98efbfa3996605b6
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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