1,2-Dichloroethane → HCID 58413049, compound

HRID 240617Notes

Reaction equation

HRID 240617 reaction equation
C(Cl)CCl.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[NH:26][C:27]2[C:28]3[C:35]([CH3:36])=[C:34]([C:37]([OH:39])=[O:38])[S:33][C:29]=3[N:30]=[CH:31][N:32]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O[N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47]>CN(C=O)C>[O:47]=[C:42]1[CH2:43][CH2:44][C:45](=[O:46])[N:41]1[O:38][C:37]([C:34]1[S:33][C:29]2[N:30]=[CH:31][N:32]=[C:27]([NH:26][C:20]3[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=3[O:18][C@H:14]3[CH2:15][CH2:16][CH2:17][N:12]([C:10]([O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[O:11])[CH2:13]3)[C:28]=2[C:35]=1[CH3:36])=[O:39]

Participants

5

Reactant 3

HCID 111,2-Dichloroethane2×HCID 80170N-Hydroxysuccinimide2×HCID 58413177HCID 58413177, compound

Product 1

HCID 58413049HCID 58413049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (290 mg) was added into a solution of 4-[2-((S)-1-tert-butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (640 mg) and N-hydroxysuccinimide (218 mg) in anhydrous DMF (10 ml). The reaction was stirred at room temperature overnight. A further aliqout of EDC (58 mg) and N-hydroxysuccinimide (44 mg) were added and the reaction stirred for further 2 h. The DMF was removed in vacuo and the residue co-evaporated from toluene. The solid was portioned between EtOAc and water. The organic layer was separated and washed with brine. The combined organics were passed through a phase separator and concentrated in vacuo.

Workup

  1. stirringthe reaction stirred for further 2 h
  2. customThe DMF was removed in vacuo
  3. customThe organic layer was separated
  4. washwashed with brine
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a67e15cbd964e55b3274c533a15cb3c
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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