3-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-fluoro-phenylamine → 1-[3-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-fluoro-phenyl]-3-{5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-urea

HRID 1818959Notes

Reaction equation

HRID 1818959 reaction equation
[CH3:1][C:2]1([CH3:17])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([NH2:16])[CH:12]=[C:13]([F:15])[CH:14]=2)[CH2:4][O:3]1.C1([O:24][C:25](=O)[NH:26][C:27]2[S:28][C:29]([CH2:32][CH2:33][NH:34][C:35]3[C:36]4[S:43][CH:42]=[CH:41][C:37]=4[N:38]=[CH:39][N:40]=3)=[CH:30][N:31]=2)C=CC=CC=1>CN(C1C=CN=CC=1)C.CS(C)=O>[CH3:1][C:2]1([CH3:17])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([NH:16][C:25]([NH:26][C:27]3[S:28][C:29]([CH2:32][CH2:33][NH:34][C:35]4[C:36]5[S:43][CH:42]=[CH:41][C:37]=5[N:38]=[CH:39][N:40]=4)=[CH:30][N:31]=3)=[O:24])[CH:12]=[C:13]([F:15])[CH:14]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 684255553-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-fluoro-phenylamineHCID 86603169{5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester

Product 1

HCID 866031851-[3-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-fluoro-phenyl]-3-{5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-urea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of compound 70.1 (1.0 mmol), compound 16.1 (1.0 mmol) and DMAP (1.0 mmol) in DMSO (10 mL) is heated at 90° C. for 30 minutes. The reaction is cooled, and partitioned between EtOAC and 1.0 N NaOH. The organic layer is separated, washed with brine, dried and concentrated to give a residue that was purified by preparative TLC (6% MeOH in dichloromethane) to provide 1-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-fluoro-phenyl]-3-{5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-urea (compound 70.2).

Workup

  1. temperatureThe reaction is cooled
  2. custompartitioned between EtOAC and 1.0 N NaOH
  3. customThe organic layer is separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto give a residue that
  8. customwas purified by preparative TLC (6% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-02b6ccd8082a484d8afca5952639b2c2
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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