Triethylamine → HCID 86619266, compound

HRID 2403422Notes

Reaction equation

HRID 2403422 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:6]2[S:11][C:10]([CH2:12][N:13]([CH3:20])[CH2:14][CH:15]3[CH2:19][CH2:18][CH2:17][NH:16]3)=[CH:9][C:7]=2[N:8]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[Cl:2][C:3]1[N:4]=[C:5]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[C:6]2[S:11][C:10]([CH2:12][N:13]([CH2:14][CH:15]3[CH2:19][CH2:18][CH2:17][N:16]3[S:35]([CH3:34])(=[O:37])=[O:36])[CH3:20])=[CH:9][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86619264HCID 86619264, compound

Product 1

HCID 86619266HCID 86619266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-pyrrolidin-2-ylmethyl-amine hydrochloride salt (380 mg) in dichloromethane (10 mL) was added triethylamine (0.30 mL) and methane sulfonyl chloride (71 μL). The mixture was stirred at room temperature for 2 h and then partitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL). The organics were washed with brine (20 mL), dried, reduced in vacuo and purified by column chromatography to give (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-(1-methanesulfonyl-pyrrolidin-2-ylmethyl)-methyl-amine as an off-white solid (124 mg).

Workup

  1. custompartitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
  2. washThe organics were washed with brine (20 mL)
  3. customdried
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-414fd0cbd95c43e7abaea2287448a368
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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