Water → HCID 86677071, compound

HRID 1520324Notes

Reaction equation

HRID 1520324 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][OH:23])[CH:18]=3)[N:13]=[C:12]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].O>C(Cl)Cl>[CH3:37][S:38]([O:23][CH2:22][CH2:21][CH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[N:11]=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67298491HCID 67298491, compound

Product 1

HCID 86677071HCID 86677071, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(4-(3-chloro-4-fluorophenylamino)-2-(pyridin-3-yl)quinazolin-6-yl)propan-1-ol (0.25 g, 0.61 mmol) and triethylamine (0.17 ml, 1.22 mmol) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (0.057 ml, 0.73 mmol). The mixture was stirred at room temperature for 1 h. Water (10 mL.) was added to the mixture and stirred for a while. The resultant precipitate was collected by filtration and washed with CH2Cl2 and dried to give 0.27 g of 3-(4-(3-chloro-4-fluorophenylamino)-2-(pyridin-3-yl)quinazolin-6-yl)propyl methanesulfonate as pale yellow solid (91%), which was used without further purification.

Workup

  1. stirringstirred for a while
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-04c989ff795f4671beb0f6ab0d0f4215
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

Loading…