4-Hydroxypyrrolidine → HCID 10293930, compound

HRID 1063172Notes

Reaction equation

HRID 1063172 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]3[CH:18]=[C:19]([C:21]([OH:23])=O)[S:20][C:13]=13)=[CH:6][CH:5]=2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:48][CH:49]1[CH2:53][CH2:52][NH:51][CH2:50]1>CN(C1C=CN=CC=1)C.CN(C=O)C>[OH:48][CH:49]1[CH2:53][CH2:52][N:51]([C:21]([C:19]2[S:20][C:13]3[C:14](=[N:15][CH:16]=[CH:17][C:12]=3[NH:11][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2]([CH3:1])=[CH:10]4)[CH:18]=2)=[O:23])[CH2:50]1

Participants

6

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22278637HCID 22278637, compound

Product 1

HCID 10293930HCID 10293930, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridine-2-carboxylic acid (0.10 g, 0.31 mmol), HATU (0.17 g, 0.46 mmol) and DMAP (0.040 g, 0.31 mmol) in DMF (3 mL) was added racemic 3-hydroxy-pyrrolidine (0.040 g, 0.46 mmol). After 3 h the reaction was quenched with a saturated aqueous solution of NaHCO3 (10 mL) and EtOAC (10 mL). The aquenched layer was further extracted with EtOAC (2×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel (CH2Cl2/MeOH 85:15) afforded the title compound as a yellow solid (0.093 g, 76%). MS: 393 (MH+); HPLC Rf: 3.41; HPLC purity: 87%.

Workup

  1. customAfter 3 h the reaction was quenched with a saturated aqueous solution of NaHCO3 (10 mL) and EtOAC (10 mL)
  2. extractionThe aquenched layer was further extracted with EtOAC (2×10 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 85:15)

Sources & evidence

ORD record
ord-f8d7791a701943289645c5655e49ece2
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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