Triethylamine → HCID 67397401, compound

HRID 1037948Notes

Reaction equation

HRID 1037948 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:34]=[C:33]1[C:41]([OH:43])=O.Cl.[NH2:45][C@@H:46]([C:48]1[S:52][C:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[CH:50][CH:49]=1)[CH3:47]>O.C(Cl)Cl>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:34]=[C:33]1[C:41]([NH:45][C@@H:46]([C:48]1[S:52][C:51]([C:53]([O:55][C:56]([CH3:57])([CH3:59])[CH3:58])=[O:54])=[CH:50][CH:49]=1)[CH3:47])=[O:43]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67397013HCID 67397013, compound

Product 1

HCID 67397401HCID 67397401, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a 2-dram vial was added triethylamine (0.156 mL, 1.12 mmol), HATU (0.106 g, 0.28 mmol), 1-benzothiophene-2-carboxylic acid (0.050 g, 0.28 mmol), and DCM (3 mL). The solution was stirred at rt for 30 min, then transferred to another 2-dram vial containing solid (R)-tert-butyl 5-(1-aminoethyl)thiophene-2-carboxylate hydrochloride. The mixture was stirred at rt for 16 h. To the reaction was then added DCM (3 mL) and water (1 mL). After separation, the aqueous layer was extracted with DCM (2×3 mL). The combined organic phases were evaporated to dryness to give (R)-tert-butyl 5-(1-(benzothiophene-2-carboxamido)ethyl)thiophene-2-carboxylate as a brown solid. LC-MS: (FA) ES+ 388.

Workup

  1. stirringThe mixture was stirred at rt for 16 h
  2. customAfter separation
  3. extractionthe aqueous layer was extracted with DCM (2×3 mL)
  4. customThe combined organic phases were evaporated to dryness

Sources & evidence

ORD record
ord-aa6be5bc336d44e4ac7fda6fa1325ce2
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

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