Triethylamine → 3-Chloro-propane-1-sulfonic acid (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-amide

HRID 2098694Notes

Reaction equation

HRID 2098694 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.C(N(CC)CC)C.[Cl:27][CH2:28][CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH3:13])[S:31]([CH2:30][CH2:29][CH2:28][Cl:27])(=[O:33])=[O:32])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 866184053-Chloro-propane-1-sulfonic acid (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-amine (220 mg) in dichloromethane (7 mL) at room temperature was added triethylamine (0.174 mL) and then 3-chloropropane sulfonyl chloride (0.134 mL). The reaction mixture was stirred at room temperature for 30 min and then quenched with water (25 mL) and extracted into dichloromethane (3×25 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give 3-chloro-propane-1-sulfonic acid (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-amide (301 mg).

Workup

  1. customquenched with water (25 mL)
  2. extractionextracted into dichloromethane (3×25 mL)
  3. washThe combined organics were washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-c9488caedc7849c1ba2dbd3fdae06f70
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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