Hydrochloric Acid → HCID 69280321, compound

HRID 901098Notes

Reaction equation

HRID 901098 reaction equation
[CH:1]([N:4]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([OH:21])=O)=[CH:13]3)[CH2:5]1)([CH3:3])[CH3:2].Cl.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]([N:4]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:21])=[CH:13]3)[CH2:5]1)([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69282936HCID 69282936, compound

Product 1

HCID 69280321HCID 69280321, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the procedure described for the synthesis of Example 1 the title compound was synthesized from 5-((S)-1-isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid 1:1 hydrochloride and pyrrolidine under coupling conditions employing TBTU and DIPEA in DMF. The crude product was purified over silica eluting with a gradient formed from DCM/MeOH(2 N NH3) 98/2 to 94/6. The product fractions were evaporated to yield the title compound as off-white solid. (m/e): 342.3 (MH+, 100%).

Workup

  1. customThe crude product was purified over silica eluting with a gradient
  2. customformed from DCM/MeOH(2 N NH3) 98/2 to 94/6
  3. customThe product fractions were evaporated

Sources & evidence

ORD record
ord-a7b094f2595c43e691528b58ef34ca67
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Reaction notes

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