4-Methoxybenzoic Acid → HCID 58465736, compound

HRID 1842468Notes

Reaction equation

HRID 1842468 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C:11]1[CH:20]=[C:14]2[CH2:15][NH:16][CH2:17][CH2:18][CH2:19][N:13]2[N:12]=1)=[O:10].[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN1CCOCC1>C(Cl)Cl>[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:16]2[CH2:17][CH2:18][CH2:19][N:13]3[N:12]=[C:11]([C:9]([NH:8][O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)=[O:10])[CH:20]=[C:14]3[CH2:15]2)=[O:28])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 74784-Methoxybenzoic AcidHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58465806HCID 58465806, compound

Product 1

HCID 58465736HCID 58465736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of N-(tetrahydro-2H-pyran-2-yloxy)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxamide (0.0283 g, 0.101 mmol) and 4-methoxybenzoic acid (0.016 g, 0.105 mmol) in methylene chloride (1 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.0434 g, 0.114 mmol) and N-methylmorpholine (0.0333 mL, 0.303 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride (2 mL) and washed with aqueous NaHCO3 (2 mL). The aqueous layer was extracted with additional methylene chloride (3 mL) and the combined organic layers concentrated to afford Intermediate 30 as a white solid.

Workup

  1. washwashed with aqueous NaHCO3 (2 mL)
  2. extractionThe aqueous layer was extracted with additional methylene chloride (3 mL)
  3. concentrationthe combined organic layers concentrated

Sources & evidence

ORD record
ord-47af6f50b2c04f1e8ec650772100cab1
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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