Diisopropylethylamine → 4-[2-[[7-Chloro-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-2-yl]amino]ethyl]-benzenesulfonamide

HRID 393191Notes

Reaction equation

HRID 393191 reaction equation
Br[C:2]1[S:3][C:4]2[C:9]([Cl:10])=[N:8][C:7]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:6][C:5]=2[N:19]=1.[NH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(N(C(C)C)C(C)C)C>O1CCCC1>[Cl:10][C:9]1[C:4]2[S:3][C:2]([NH:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([S:29]([NH2:32])(=[O:30])=[O:31])=[CH:27][CH:28]=3)=[N:19][C:5]=2[N:6]=[C:7]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 220520385-(Benzylthio)-2-bromo-7-chlorothiazolo[4,5-d]pyrimidine

Product 1

HCID 226490154-[2-[[7-Chloro-5-[(phenylmethyl)thio]thiazolo[4,5-d]pyrimidin-2-yl]amino]ethyl]-benzenesulfonamideYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 219 (0.3 g) in tetrahydrofuran (2 ml) containing 4-(2-aminoethyl)benzenesulfonamide (0.161 g) and N-ethyldiisopropylamine (0.5 ml) was stirred for 16 hours. The mixture was evaporated to dryness then purified (SiO2, ethyl acetate:dichloromethane 4:6 as eluant) to give the title compound (310 mg).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthen purified (SiO2, ethyl acetate:dichloromethane 4:6 as eluant)

Sources & evidence

ORD record
ord-3c51001c0d2447609ac10a00ff064941
Source dataset
uspto-grants-2004_10
Patent number
US06806273B1

Reaction notes

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