Triethylamine → HCID 59380001, compound

HRID 2353644Notes

Reaction equation

HRID 2353644 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:6]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[N:4]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:15][C@H:10]1[CH2:11][O:12][CH2:13][CH2:14][N:9]1[C:7]1[CH:8]=[C:3]([CH2:2][O:1][S:40]([CH3:39])(=[O:42])=[O:41])[N:4]=[C:5]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:24])=[CH:20][CH:21]=2)[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59379926HCID 59379926, compound

Product 1

HCID 59380001HCID 59380001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-[4-(Hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-phenyl-urea (388 mg) was dissolved in DCM (15 mL) and triethylamine (0.194 mL) and the solution was cooled to 0° C. Methanesulfonyl chloride (0.108 mL) was added and the reaction stirred for 90 mins at 0° C. The reaction mixture was concentrated in vacuo and partitioned between DCM (20 mL) and water (10 mL). The organic phase was washed with brine (10 mL), dried (MgSO4) and concentrated in vacuo to give the desired compound (273 mg) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between DCM (20 mL) and water (10 mL)
  3. washThe organic phase was washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18db2c90791f47febd139656e89309ca
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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