Acetic Acid → HCID 178496622, compound

HRID 406089Notes

Reaction equation

HRID 406089 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[CH:16][CH2:17][CH2:18][NH:19][C:20]([C:22]1[S:47][C:25]2[N:26]=[CH:27][N:28]=[C:29]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[O:38][C@H:39]3[CH2:44][CH2:43][C@H:42]([O:45][CH3:46])[CH2:41][CH2:40]3)[C:24]=2[C:23]=1[CH3:48])=[O:21].[NH:49]1[CH2:53][CH2:52][CH:51]([OH:54])[CH2:50]1.C(O)(=O)C>C(Cl)Cl>[OH:54][CH:51]1[CH2:52][CH2:53][N:49]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([C:22]2[S:47][C:25]3[N:26]=[CH:27][N:28]=[C:29]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=4[O:38][C@H:39]4[CH2:44][CH2:43][C@H:42]([O:45][CH3:46])[CH2:41][CH2:40]4)[C:24]=3[C:23]=2[CH3:48])=[O:21])[CH2:50]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 982104-HydroxypyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 178496624HCID 178496624, compound

Product 1

HCID 178496622HCID 178496622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.155 g sodium triacetoxyborohydride were added to a solution of the 0.21 g 4-[4-fluoro-2-(trans-4-methoxy-cyclohexyloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (3-oxo-propyl)-amide and 43 μl 3-pyrrolidinol in methylene chloride followed by addition of 49 μl acetic acid. The mixture was stirred at rt overnight, diluted with methylene chloride and then washed with 10% aq. K2CO3. The mixture was passed through a hydrophobic frit. The filtrate was evaporated and purified by chromatography.

Workup

  1. washwashed with 10% aq. K2CO3
  2. customThe filtrate was evaporated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-222a81b6949a48a7b033ece438d2ee86
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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