Morpholine → HCID 59380159, compound

HRID 2353677Notes

Reaction equation

HRID 2353677 reaction equation
OC[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.[CH2:32]([N:34]([CH2:37][CH3:38])[CH2:35]C)[CH3:33].CS(Cl)(=O)=[O:41].N1CCOCC1>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]([CH2:35][N:34]2[CH2:37][CH2:38][O:41][CH2:33][CH2:32]2)[N:4]=[C:5]([C:16]2[CH:21]=[CH:20][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:18][CH:17]=2)[N:6]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59379926HCID 59379926, compound

Product 1

HCID 59380159HCID 59380159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-[4-(Hydroxymethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-phenyl-urea (90 mg) was dissolved in DCM (5 mL) and triethylamine (0.045 mL) and the solution cooled to 0° C. Methane sulfonyl chloride (0.026 mL) was added and the reaction stirred for 1 h at RT. Morpholine (0.2 mL) was added and the reaction was left at RT for 72 hours before being concentrated in vacuo and purified by prep-HPLC (basic) to give the desired compound (64 mg) as a white solid.

Workup

  1. waitthe reaction was left at RT for 72 hours
  2. concentrationbefore being concentrated in vacuo
  3. custompurified by prep-HPLC (basic)

Sources & evidence

ORD record
ord-97fa40a409a54dfdb80cda50fd18eb8b
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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