Diisopropylethylamine → 3-[[2-amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-hydroxy-(3R,4R)-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester

HRID 1097346Notes

Reaction equation

HRID 1097346 reaction equation
[NH2:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C(N(C(C)C)CC)(C)C.Cl[C:25]1[C:26]2[S:43][C:42]([NH2:44])=[N:41][C:27]=2[N:28]=[C:29]([S:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[F:40])[N:30]=1>CN1C(=O)CCC1>[NH2:44][C:42]1[S:43][C:26]2[C:25]([NH:1][C@H:2]3[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]3)=[N:30][C:29]([S:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=3[F:40])=[N:28][C:27]=2[N:41]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112216507-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]-thiazolo[4,5-d]pyrimidin-2-amineHCID 11275699(3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidine

Product 1

HCID 866358013-[[2-amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-hydroxy-(3R,4R)-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(3R,4R)-3-Amino-4-hydroxy-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (0.73 g), diisopropylethylamine (1.0 ml) and the product of example 4 step b), were stirred in NMP (10 ml) at 100° C. for 28 hrs. The cooled mixture was poured onto water and the solid produced collected, washed with water and air dried. The crude material was purified (SiO2, ethyl acetate as eluant) to give the subtitle compound as a colourless solid (0.58 g).

Workup

  1. additionThe cooled mixture was poured onto water
  2. customthe solid produced
  3. customcollected
  4. washwashed with water and air
  5. customdried
  6. customThe crude material was purified (SiO2, ethyl acetate as eluant)

Sources & evidence

ORD record
ord-47af231b0a5f4e05844c4722b8953b34
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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