2-Thiophenecarboxylic acid → HCID 10140232, compound

HRID 892007Notes

Reaction equation

HRID 892007 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[O:49][CH2:50][CH:51]([OH:66])[CH2:52][N:53]1[CH2:57][CH2:56][CH:55]([O:58][C:59]2[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=2)[CH2:54]1>CN1C(=O)CCC1.N1C=CC=CC=1>[Cl:65][C:62]1[CH:61]=[CH:60][C:59]([O:58][CH:55]2[CH2:56][CH2:57][N:53]([CH2:52][CH:51]([OH:66])[CH2:50][O:49][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[NH:42][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:8])[CH2:54]2)=[CH:64][CH:63]=1

Participants

7

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22241235HCID 22241235, compound

Product 1

HCID 10140232HCID 10140232, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of 80 uL 0.2M 2-thiophenecarboxylic acid in NMP were HBTU (80 uL, 0.2M/NMP), HoBT (80 uL, 0.2M/NMP), DIEA (30 uL, 0.5M/NMP) and pyridine (30 uL, 0.5M/NMP) added and stirred for 30 minutes before 1-[(2-aminophenyl)oxy]-3-{3-[(4-chlorophenyl)oxy]-1-pyrrolidinyl}-2-propanol (75 uL, 0.2M/NMP) was added. The mixture was stirred overnight at room temperature before it was concentrated under reduced pressure to dryness. The product was diluted with 1000 uL dichloromethane and washed with with sat.NaHCO3/aq (800 uL), 1.81% HCl/aq(800 uL) and sat. NaCl/aq. The organic layer was concentrated under reduced pressure to dryness and used without further purification. Yield 3.6mg, 51%

Workup

  1. additionadded
  2. additionwas added
  3. concentrationwas concentrated under reduced pressure to dryness
  4. additionThe product was diluted with 1000 uL dichloromethane
  5. washwashed with
  6. concentrationThe organic layer was concentrated under reduced pressure to dryness
  7. customused without further purification

Sources & evidence

ORD record
ord-3b69685bf58549f4b5d92474093ce381
Source dataset
uspto-grants-2006_02
Patent number
US07005439B2

Reaction notes

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