4-Methylmorpholine → HCID 58465597, compound

HRID 1842469Notes

Reaction equation

HRID 1842469 reaction equation
[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:4]2=[CH:3][C:2]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[S:26][C:25]([C:27](O)=[O:28])=[CH:24][CH:23]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN1CCOCC1>C(Cl)Cl>[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[S:26][C:25]([C:27]([N:9]2[CH2:8][CH2:7][CH2:6][N:5]3[N:1]=[C:2]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=[C:4]3[CH2:10]2)=[O:28])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 7364825-(Pyridin-2-yl)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 58465821HCID 58465821, compound

Product 1

HCID 58465597HCID 58465597, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of ethyl 5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate (0.033 g, 0.16 mmol) and 5-(2-pyridyl)thiophene-2-carboxylic acid (0.036 g, 0.18 mmol) in methylene chloride (1 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.07 g, 0.184 mmol) and N-methylmorpholine (0.053 mL, 0.48 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with methylene chloride (3 mL) and washed with saturated aqueous NaHCO3 (2 mL). The aqueous layer was extracted with additional methylene chloride (3 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to dryness to afford Intermediate 31.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2 mL)
  2. extractionThe aqueous layer was extracted with additional methylene chloride (3 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ce79fd6a70d04a61afaa73b82fefe903
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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