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 1006497Notes

Reaction equation

HRID 1006497 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 is 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-315279f4d83b4167b1a51212e65b7238
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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